Socher, Elke’s team published research in Organic & Biomolecular Chemistry in 10 | CAS: 169396-92-3

Organic & Biomolecular Chemistry published new progress about 169396-92-3. 169396-92-3 belongs to pyrimidines, auxiliary class Pyrimidine,Carboxylic acid,Amine,Amide,Others,PNA, name is 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetamido)acetic acid, and the molecular formula is C14H14N2O2, Quality Control of 169396-92-3.

Socher, Elke published the artcileDual fluorophore PNA FIT-probes – extremely responsive and bright hybridization probes for the sensitive detection of DNA and RNA, Quality Control of 169396-92-3, the publication is Organic & Biomolecular Chemistry (2012), 10(36), 7363-7371, database is CAplus and MEDLINE.

Fluorescently labeled oligonucleotides are commonly employed as probes to detect specific DNA or RNA sequences in homogeneous solution Useful probes should experience strong increases in fluorescent emission upon hybridization with the target. Dual labeled peptide nucleic acid probes were developed which signal the presence of complementary DNA or RNA by up to 450-fold enhancements of fluorescence intensity. This enabled the very sensitive detection of a DNA target (40 pM LOD), which was detectable at less than 0.1% of the beacon concentration In contrast to existing DNA-based mol. beacons, this PNA-based method does not require a stem sequence to enforce dye-dye communication. Rather, the method relies on the energy transfer between a “smart” thiazole orange (TO) nucleotide, which requires formation of the probe-target complex in order to become fluorescent, and terminally appended acceptor dyes. To improve upon fluorescence responsiveness the energy pathways were dissected. Hydrophobic, spectrally mismatched dye combinations allowed significant (99.97%) decreases of background emission in the absence of a target. By contrast, spectral overlap between TO donor emission and acceptor excitation enabled extremely bright FRET signals. This and the large apparent Stokes shift (82 nm) suggests potential applications in the detection of specific RNA targets in biogenic matrixes without the need of sample pre-processing prior to detection.

Organic & Biomolecular Chemistry published new progress about 169396-92-3. 169396-92-3 belongs to pyrimidines, auxiliary class Pyrimidine,Carboxylic acid,Amine,Amide,Others,PNA, name is 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetamido)acetic acid, and the molecular formula is C14H14N2O2, Quality Control of 169396-92-3.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Kummer, Susann’s team published research in Angewandte Chemie, International Edition in 50 | CAS: 186046-81-1

Angewandte Chemie, International Edition published new progress about 186046-81-1. 186046-81-1 belongs to pyrimidines, auxiliary class Pyrimidine,Carboxylic acid,Amine,Benzene,Amide,Others,PNA,, name is 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(4-(((benzhydryloxy)carbonyl)amino)-2-oxopyrimidin-1(2H)-yl)acetamido)acetic acid, and the molecular formula is C39H35N5O8, Computed Properties of 186046-81-1.

Kummer, Susann published the artcileFluorescence imaging of influenza H1N1 mRNA in living infected cells using single-chromophore FIT-PNA, Computed Properties of 186046-81-1, the publication is Angewandte Chemie, International Edition (2011), 50(8), 1931-1934, S1931/1-S1931/22, database is CAplus and MEDLINE.

The FIT-PNA probes used in this work contain a single thiazole orange (TO) intercalator serving as artificial fluorescent nucleobase. These probes respond to changes of the local structure in the vicinity of the dye rather than to the more global changes of conformation that confer fluorescence signaling by dual-labeled mol. beacons. Herein we demonstrate the advantageous properties of FIT-PNA probes in the imaging of mRNA from an influenza virus strain belonging to the same subtype as the recently emerged swine virus (A/Mexico/1/2009, H1N1).

Angewandte Chemie, International Edition published new progress about 186046-81-1. 186046-81-1 belongs to pyrimidines, auxiliary class Pyrimidine,Carboxylic acid,Amine,Benzene,Amide,Others,PNA,, name is 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(4-(((benzhydryloxy)carbonyl)amino)-2-oxopyrimidin-1(2H)-yl)acetamido)acetic acid, and the molecular formula is C39H35N5O8, Computed Properties of 186046-81-1.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Kummer, Susann’s team published research in Bioconjugate Chemistry in 23 | CAS: 186046-81-1

Bioconjugate Chemistry published new progress about 186046-81-1. 186046-81-1 belongs to pyrimidines, auxiliary class Pyrimidine,Carboxylic acid,Amine,Benzene,Amide,Others,PNA,, name is 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(4-(((benzhydryloxy)carbonyl)amino)-2-oxopyrimidin-1(2H)-yl)acetamido)acetic acid, and the molecular formula is C39H35N5O8, COA of Formula: C39H35N5O8.

Kummer, Susann published the artcilePNA FIT-Probes for the Dual Color Imaging of Two Viral mRNA Targets in Influenza H1N1 Infected Live Cells, COA of Formula: C39H35N5O8, the publication is Bioconjugate Chemistry (2012), 23(10), 2051-2060, database is CAplus and MEDLINE.

Fluorogenic hybridization probes that allow RNA imaging provide information as to how the synthesis and transport of particular RNA mols. is orchestrated in living cells. The authors explored the peptide nucleic acid (PNA)-based FIT-probes in the simultaneous imaging of two different viral mRNA mols. expressed during the replication cycle of the H1N1 influenza A virus. PNA FIT-probes are non-nucleotidic, nonstructured probes and contain a single asym. cyanine dye which serves as a fluorescent base surrogate. The fluorochrome acts as a local intercalator probe and reports hybridization of target DNA/RNA by enhancement of fluorescence. Though multiplexed hybridization probes are expected to facilitate the anal. of RNA expression, there are no previous reports on the dual color imaging of two different viral mRNA targets. The authors developed a set of two differently colored PNA FIT-probes that allow the spectrally resolved imaging of mRNA coding for neuraminidase (NA) and matrix protein 1 (M1); proteins which execute distinct functions during the replication of the influenza A virus. The probes were characterized by a wide range of applicable hybridization temperatures The same probe sequence enabled live-cell RNA imaging (at 37°) as well as real-time PCR measurements (at 60° annealing temperature). This facilitated a comprehensive anal. of RNA expression by quant. (qPCR) and qual. (imaging) means. Confocal laser scanning microscopy showed that the viral-RNA specific PNA FIT-probes neither stained noninfected cells nor cells infected by a control virus. The joint use of differently colored PNA FIT-probes in this feasibility study revealed significant differences in the expression pattern of influenza H1N1 mRNAs coding for NA or M1. These experiments provide evidence for the usefulness of PNA FIT-probes in studies on the temporal and spatial progression of mRNA synthesis in living cells for two mRNA species.

Bioconjugate Chemistry published new progress about 186046-81-1. 186046-81-1 belongs to pyrimidines, auxiliary class Pyrimidine,Carboxylic acid,Amine,Benzene,Amide,Others,PNA,, name is 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(4-(((benzhydryloxy)carbonyl)amino)-2-oxopyrimidin-1(2H)-yl)acetamido)acetic acid, and the molecular formula is C39H35N5O8, COA of Formula: C39H35N5O8.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Kummer, Susann’s team published research in Angewandte Chemie, International Edition in 50 | CAS: 169396-92-3

Angewandte Chemie, International Edition published new progress about 169396-92-3. 169396-92-3 belongs to pyrimidines, auxiliary class Pyrimidine,Carboxylic acid,Amine,Amide,Others,PNA, name is 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetamido)acetic acid, and the molecular formula is C26H26N4O7, Safety of 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetamido)acetic acid.

Kummer, Susann published the artcileFluorescence imaging of influenza H1N1 mRNA in living infected cells using single-chromophore FIT-PNA, Safety of 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetamido)acetic acid, the publication is Angewandte Chemie, International Edition (2011), 50(8), 1931-1934, S1931/1-S1931/22, database is CAplus and MEDLINE.

The FIT-PNA probes used in this work contain a single thiazole orange (TO) intercalator serving as artificial fluorescent nucleobase. These probes respond to changes of the local structure in the vicinity of the dye rather than to the more global changes of conformation that confer fluorescence signaling by dual-labeled mol. beacons. Herein we demonstrate the advantageous properties of FIT-PNA probes in the imaging of mRNA from an influenza virus strain belonging to the same subtype as the recently emerged swine virus (A/Mexico/1/2009, H1N1).

Angewandte Chemie, International Edition published new progress about 169396-92-3. 169396-92-3 belongs to pyrimidines, auxiliary class Pyrimidine,Carboxylic acid,Amine,Amide,Others,PNA, name is 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetamido)acetic acid, and the molecular formula is C26H26N4O7, Safety of 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetamido)acetic acid.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Kummer, Susann’s team published research in Bioconjugate Chemistry in 23 | CAS: 169396-92-3

Bioconjugate Chemistry published new progress about 169396-92-3. 169396-92-3 belongs to pyrimidines, auxiliary class Pyrimidine,Carboxylic acid,Amine,Amide,Others,PNA, name is 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetamido)acetic acid, and the molecular formula is C26H26N4O7, Synthetic Route of 169396-92-3.

Kummer, Susann published the artcilePNA FIT-Probes for the Dual Color Imaging of Two Viral mRNA Targets in Influenza H1N1 Infected Live Cells, Synthetic Route of 169396-92-3, the publication is Bioconjugate Chemistry (2012), 23(10), 2051-2060, database is CAplus and MEDLINE.

Fluorogenic hybridization probes that allow RNA imaging provide information as to how the synthesis and transport of particular RNA mols. is orchestrated in living cells. The authors explored the peptide nucleic acid (PNA)-based FIT-probes in the simultaneous imaging of two different viral mRNA mols. expressed during the replication cycle of the H1N1 influenza A virus. PNA FIT-probes are non-nucleotidic, nonstructured probes and contain a single asym. cyanine dye which serves as a fluorescent base surrogate. The fluorochrome acts as a local intercalator probe and reports hybridization of target DNA/RNA by enhancement of fluorescence. Though multiplexed hybridization probes are expected to facilitate the anal. of RNA expression, there are no previous reports on the dual color imaging of two different viral mRNA targets. The authors developed a set of two differently colored PNA FIT-probes that allow the spectrally resolved imaging of mRNA coding for neuraminidase (NA) and matrix protein 1 (M1); proteins which execute distinct functions during the replication of the influenza A virus. The probes were characterized by a wide range of applicable hybridization temperatures The same probe sequence enabled live-cell RNA imaging (at 37°) as well as real-time PCR measurements (at 60° annealing temperature). This facilitated a comprehensive anal. of RNA expression by quant. (qPCR) and qual. (imaging) means. Confocal laser scanning microscopy showed that the viral-RNA specific PNA FIT-probes neither stained noninfected cells nor cells infected by a control virus. The joint use of differently colored PNA FIT-probes in this feasibility study revealed significant differences in the expression pattern of influenza H1N1 mRNAs coding for NA or M1. These experiments provide evidence for the usefulness of PNA FIT-probes in studies on the temporal and spatial progression of mRNA synthesis in living cells for two mRNA species.

Bioconjugate Chemistry published new progress about 169396-92-3. 169396-92-3 belongs to pyrimidines, auxiliary class Pyrimidine,Carboxylic acid,Amine,Amide,Others,PNA, name is 2-(N-(2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)ethyl)-2-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetamido)acetic acid, and the molecular formula is C26H26N4O7, Synthetic Route of 169396-92-3.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Iltzsch, Max H.’s team published research in Biochemical Pharmacology in 46 | CAS: 608-34-4

Biochemical Pharmacology published new progress about 608-34-4. 608-34-4 belongs to pyrimidines, auxiliary class Pyrimidine,Amide, name is 3-Methylpyrimidine-2,4(1H,3H)-dione, and the molecular formula is C5H6N2O2, Formula: C5H6N2O2.

Iltzsch, Max H. published the artcileStructure-activity relationship of nucleobase ligands of uridine phosphorylase from Toxoplasma gondii, Formula: C5H6N2O2, the publication is Biochemical Pharmacology (1993), 46(10), 1849-58, database is CAplus and MEDLINE.

Seventy-nine nucleobase analogs were evaluated as potential inhibitors of T. gondii uridine phosphorylase (UrdPase), and the apparent Ki (appKi) values for these compounds were determined Based on the inhibition data, a structure-activity relationship for the binding of nucleobase analogs to the enzyme was formulated, using uracil as a reference compound Two compounds were identified as very potent inhibitors of T. gondii UrdPase: 5-benzyloxybenzylbarbituric acid and 5-benzyloxybenzyluracil, which had appKi values of 0.32 and 2.5 μM, resp. A comparison of the results from the present study with those from similar studies on mammalian UrdPase and thymidine phosphorylase (dThdPase) revealed that there are both similarities and differences between the catalytic site of T. gondii UrdPase and the catalytic sites of the mammalian enzymes with respect to binding of uracil analogs. One compound, 6-benzyl-2-thiouracil, was identified as a potent, specific inhibitor (appKi = 14 μM) of T. gondii UrdPase, relative to mammalian UrdPase and dThdPase.

Biochemical Pharmacology published new progress about 608-34-4. 608-34-4 belongs to pyrimidines, auxiliary class Pyrimidine,Amide, name is 3-Methylpyrimidine-2,4(1H,3H)-dione, and the molecular formula is C5H6N2O2, Formula: C5H6N2O2.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Sugiyama, Toru’s team published research in Nucleic Acids Research Supplement in 2 | CAS: 172405-16-2

Nucleic Acids Research Supplement published new progress about 172405-16-2. 172405-16-2 belongs to pyrimidines, auxiliary class Pyrimidine,Carboxylic acid,Amine,Amide, name is 2-(4-((tert-Butoxycarbonyl)amino)-2-oxopyrimidin-1(2H)-yl)acetic acid, and the molecular formula is C4H4N2O2, COA of Formula: C11H15N3O5.

Sugiyama, Toru published the artcileSynthesis of PNA using a Fmoc/Boc protecting group strategy, COA of Formula: C11H15N3O5, the publication is Nucleic Acids Research Supplement (2002), 145-146, database is CAplus.

A symposium on the authors’ work. Syntheses of PNA monomers whose nucleobases are protected with Boc group are described. To overcome the solubility problem of carboxymethyl-guanine derivative, the 2-trimethylsilylethyl group was introduced at O6 as a second protecting group.

Nucleic Acids Research Supplement published new progress about 172405-16-2. 172405-16-2 belongs to pyrimidines, auxiliary class Pyrimidine,Carboxylic acid,Amine,Amide, name is 2-(4-((tert-Butoxycarbonyl)amino)-2-oxopyrimidin-1(2H)-yl)acetic acid, and the molecular formula is C4H4N2O2, COA of Formula: C11H15N3O5.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Almeida, D.’s team published research in Physical Chemistry Chemical Physics in 15 | CAS: 608-34-4

Physical Chemistry Chemical Physics published new progress about 608-34-4. 608-34-4 belongs to pyrimidines, auxiliary class Pyrimidine,Amide, name is 3-Methylpyrimidine-2,4(1H,3H)-dione, and the molecular formula is C5H6N2O2, Computed Properties of 608-34-4.

Almeida, D. published the artcileN-site de-methylation in pyrimidine bases as studied by low energy electrons and ab initio calculations, Computed Properties of 608-34-4, the publication is Physical Chemistry Chemical Physics (2013), 15(27), 11431-11440, database is CAplus and MEDLINE.

Electron transfer and dissociative electron attachment to 3-methyluracil (3meU) and 1-methylthymine (1meT) yielding anion formation were studied in atom-mol. collision and electron attachment experiments, resp. The former was studied in the collision energy range 14-100 eV whereas the latter in the 0-15 eV incident electron energy range. In the present studies, emphasis is given to the reaction channel resulting in the loss of the Me group from the N-sites with the extra charge located on the pyrimidine ring. This particular reaction channel has neither been approached in the context of dissociative electron attachment nor in atom-mol. collisions yet. Quantum chem. calculations were performed to provide some insight into the dissociation mechanism involved along the N-CH3 bond reaction coordinate. The calculations provide support to the threshold value derived from the electron transfer measurements, allowing for a better understanding of the role of the potassium cation as a stabilizing agent in the collision complex. The present comparative study gives insight into the dynamics of the decaying transient anion and more precisely into the competition between dissociation and auto-detachment.

Physical Chemistry Chemical Physics published new progress about 608-34-4. 608-34-4 belongs to pyrimidines, auxiliary class Pyrimidine,Amide, name is 3-Methylpyrimidine-2,4(1H,3H)-dione, and the molecular formula is C5H6N2O2, Computed Properties of 608-34-4.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

King, F. E.’s team published research in Journal of the Chemical Society in | CAS: 5738-14-7

Journal of the Chemical Society published new progress about 5738-14-7. 5738-14-7 belongs to pyrimidines, auxiliary class Pyrimidine,Amine,Alcohol,Pyrimidine, name is 2-(Dimethylamino)pyrimidine-4,6-diol, and the molecular formula is C6H9N3O2, Application of 2-(Dimethylamino)pyrimidine-4,6-diol.

King, F. E. published the artcileNew potential chemotherapeutic agents. VI. Derivatives of 2,4-diazaacridine, Application of 2-(Dimethylamino)pyrimidine-4,6-diol, the publication is Journal of the Chemical Society (1947), 726-34, database is CAplus and MEDLINE.

cf. C.A. 41, 3107d. Because of the interest in chemotherapy in compounds having a structural resemblance to riboflavin, attention has been turned to 2′,3′,4,5-quinolinopyrimidine, which has been designated 2,4-diazaacridine (cf. Conrad and Reinbach, Ber. 34, 1341(1901)), and especially to derivatives containing basic side chains. Mercaptobarbituric acid (I) (5 g.), 4.5 g. Et2N(CH2)3NH2, and about 2 mols. freshly prepared Pb(OH)2 in iso-AmOH, refluxed 15 hrs., give 78% 2-(3-diethylaminopropylamino)-4,6-dihydroxypyrimidine (II), analyzed as the picrolonate, with 1 mol. H2O (0.5 mol. lost at 100°, 1 mol. at 150°), yellow, m. 235° (decomposition). I (14.4 g.) and 8.4 g. NaHCO3 in 200 cc. H2O, shaken 30 min. with 12.6 g. Me2SO4 at room temperature, give 72% 4,6-dihydroxy-2-methylmercaptopyrimidine (III); 10 g. crude III and 3.9 g. Et2N(CH2)3NH2, heated 30 min. at 180°, give 92% II. EtO2CCH2CH2COCl (6 g.) and 5.2 g. Et2N(CH2)3NH2 in ether at 0° give 60% α-carbethoxy N-(3-diethylaminopropyl)acetamide, b0.05 115°, did not react with CO(NH2)2 in the presence of EtONa in EtOH (6 hrs.). EtO2CCH2C(OEt):NH.HCl (6 g.) and 4.2 g. Et2N(CH2)3NH2 in 100 cc. EtOH 12 hrs. at room temperature give Et2N(CH2)3NHC(:NH)CH2CO2Et, whose picrolonate, with 1 mol. H2O, yellow, m. 125-30°; this could not be condensed with H2NCO2Et. The action of Et2N(CH2)3NH2 on EtO2CCH2CONHCONH2 gives barbituric acid and not Et2N(CH2)2NHCOCH2CONHCONH2, which might have been cyclized to a pyrimidine. 2,4,6-Trichloropyrimidine (IV) (3 g.), added to 11 g. PhCH2OH and 1.15 g. Na in 100 cc. PhMe (after formation of the alcoholate) and the mixture refluxed 2 hrs., gives 63% of the 2,4,6-tris(benzyloxy) derivative, m. 62-4°; the action of Na in liquid NH3 does not give a pure compound; hydrogenation in AcOH over Pd-charcoal gives 84% barbituric acid. IV (18 g.) in 100 cc. Me2CO, cautiously treated with 13 g. Et2N(CH2)3NH2 with cooling, gives 72% 2,6-dichloro-4-(3-diethylaminopropylamino)pyrimidine (V); HCl salt m. 149°; picrate, bright yellow, m. 162°; picrolonate, yellow, m. 164°. V (3.1 g.) and 10 cc. concentrated HCl, heated on the steam bath 12 hrs., give 76% of the di-HCl salt, m. 253° (decomposition), of 6-chloro-4-(3-diethylaminopropylamino)-2-hydroxypyrimidine; picrate, yellow, m. 209° (decomposition). V (6.25 g.), added in 10 portions to PhCH2ONa (from 13 g. PhCH2OH and 1.4 g. Na) in 100 cc. PhMe and the mixture heated 2 hrs., gives 80% 4-(3-diethylaminopropylamino)-2,6-bis(benzyloxy)pyrimidine (VI), m. 68° (dipicrate, m. 156°); crude VI in AcOH, hydrogenated over Pd-charcoal at room temperature and atm. pressure (4 hrs.), gives 4-(3-diethylaminopropylamino)-2,6-dihydroxypyrimidine (VII), apparently with 3 mols. AcOH, very hygroscopic; picrolonate m. 186° (decomposition); 1 of the 2 mols. of H2O is lost at 100° and the 2nd at 130°. VII and p-ClC6H4N2Cl give 57% of the 5-(p-chlorophenylazo) derivative, with 2 mols. H2O (1 lost at 100°), yellow, m. 151° (decomposition) (dipicrate, m. 205° (decomposition)); catalytic reduction over RaneyNi gives a product rapidly oxidized in the air. Although VII was devoid of antimalarial activity, the 5-Me analog was also prepared but it was also inactive. 2,4,6-Trichloro-5-methylpyrimidine (19.7 g.) in 100 cc. Me2CO, cautiously treated with 13 g. Et2N(CH2)3NH2 in 100 cc. Me2CO and cooled to 4°, gives 60% of the HCl salt (VIII), m. 193-5°, of 2,6-dichloro-4-(3-diethylaminopropylamino)-5-methylpyrimidine, whose picrate m. 163°. VIII and PhCH2ONa give the 2,6-bis(benzyloxy) derivative (IX), an oil (tripicrate, m. 141-2°). Hydrogenation of IX in AcOH over Pd-charcoal at room temperature and atm. pressure gives 7.2 g. 4-(3-diethylaminopropylamino)-2,6-dihydroxy-5-methylpyrimidine, as the triacetate (with 1 mol. H2O); dipicrate, yellow, m. 183-4° (decomposition); picrolonate, yellow, m. 223° (decomposition). 4,6-Dichloro-2-methylaminopyrimidine (X) (4.4 g.) and PhCH2ONa (from 1.15 g. Na) in 150 cc. PhMe, heated 1 hr. at 100°, give 27.5% 4-chloro-2-methylamino-6-(benzyloxy)pyrimidine, m. 120°; if the reaction mixture is refluxed 4 hrs., there results 61% 2-methylamino-4,6-bis(benzyloxy)pyrimidine, m. 101°; reduction (8 hrs.) in AcOH over Pd-charcoal gives 66.6% 2-methylamino-4,6-dihydroxypyrimidine (XI), with 0.5 mol. EtOH and 2/3 mols. H2O, m. above 310°. 2,6-Dichloro-4-methylaminopyrimidine (6 g.) and PhCH2ONa in 75 cc. PhMe, refluxed 3 hrs., give 69% 4-methylamino-2,6-bis(benzyloxy)pyrimidine, m. 118°; reduction (2.5 hrs.) in AcOH gives 98.8% 4-methylamino-2,6-dihydroxypyrimidine (XIA), m. 302° (decomposition). IV (15 g.) and 27 cc. 33% Me2NH in 75 cc. EtOH give 48% 2,6-dichloro-4-dimethylaminopyrimidine (XII), m. 113°; with PhCH2ONa in PhMe (refluxed 1 hr.), there results 69.5% 4-dimethylamino-2,6-bis(benzyloxy)pyrimidine, m. 79°; catalytic reduction gives 77% 4-dimethylamino-2,6-dihydroxypyrimidine, m. 320° (decomposition). The alc. mother liquor from XII yields 35% 4,6-dichloro-2-dimethylaminopyrimidine (XIII), m. 102-3°. XIII (3.5 g.) and PhCH2ONa (from 0.84 g. Na) in 50 cc. PhMe, heated 1 hr. at 100°, give 73% 4-chloro-2-dimethylamino-6-(benzyloxy)pyrimidine, m. 84°; when refluxed 3 hrs., there results 69.5% 2-dimethylamino-4,6-bis(benzyloxy)pyrimidine, whose picrate, yellow, m. 176°; catalytic reduction gives 73% 2-dimethylamino-4,6-dihydroxypyrimidine, yellow, m. 320° (decomposition). IV (5.75 g.) in 90 cc. Me2CO and the NH:C(NH2)2 from 6 g. of the HCl salt in 10 cc. H2O, on standing 15 min., give 53% 2,6-dichloro-4-guanidinopyrimidine, m. 325° (decomposition); the mother liquor apparently contains an addnl. 43%; PhCH2ONa in PhMe, heated 2 hrs. at 100°, gives 61% 6-chloro-4-guanidino-2-(benzyloxy)pyrimidine, m. 170° (picrate, yellow, m. 250° (decomposition)); refluxed in PhMe 8 hrs., there results 78% 4-guanidino-2,6-bis(benzyloxy)pyrimidine, characterized as the picrate, m. 200°; reduction yields 38% 4-guanidino-2,6-dihydroxypyrimidine (XIV), m. 300°. Malonylguanidine, CH:C(OH).N:C(NH2).N:C(OH), (2 g.) and 3 g. o-H2NC6H4CHO in 100 cc. H2O containing 5 cc. HCl, heated 1 hr. on the steam bath, give 69.5% 3-amino-1-hydroxy-2,4-diazaacridine, analyzed as the HCl salt (with 2 mols. H2O), m. above 310°; the free base, m. above 310°, gives a pale yellow solution in NaOH with a strong greenish blue fluorescence. 4-Amino-2,6-dihydroxypyrimidine and o-H2NC6H4CHO give 61% 1,3-dihydroxy-2,4-diazaacridine (XV) (cf. Conrad and Reinbach, loc. cit.), which crystallizes with 1 mol. AcOH. 2,4-Diamino-6-hydroxypyrimidine (3 g.) in 100 cc. H2O and 10 cc. AcOH, treated with 3 g. o-H2NC6H4CHO in 10 cc. EtOH and refluxed 30 min., gives 35% (XVI) with 0.5 mol. H2O, bright yellow, m. above 330°; its solutions exhibit a vivid blue fluorescence; HCl salt, biscuit-colored, m. above 310°. XI and o-H2NC6H4CHO give 63.5% 3-methylamino-1-hydroxy-2,4-diazaacridine, with 4/3 mols. H2O, pale yellow, m. above 310°; its solutions have a marked green-blue fluorescence; XIA gives XV. XIV gives 81% of the 1-guanidino analog of XV, m. above 310°; di-HCl salt, with 1.5 mols. H2O, m. above 310°; at 120° it forms the mono-HCl salt, with 1 mol. H2O; picrate, yellow, with 1.5 mols. H2O, m. 230° (decomposition). The 3-(3-diethylaminopropylamino) analog of XV, obtained as a reddish oil, analyzed as the meconate (50% yield), with 5 mols. H2O (2.5 mols. lost at 100°), pale yellow, m. 180° (decomposition); the picrate, with 1 mol. EtOH, m. 222° (decomposition) and could not be further purified. Barbituric acid (3.9 g.) and 3.9 g. 2,4-(O2N)2C6H3CHO in 150 cc. boiling H2O give 71.5 g. of the 2,4-dinitrobenzylidene derivative, orange, m. above 310°; 2,4-H2N(O2N)C6H3CHO in dilute EtOH gives 64.5% 6-nitro-1,3-dihydroxy-2,4-diazaacridine, with 1 mol. EtOH, cream, m. above 310°; it forms an orange Na salt; in AcOH, it shows a blue fluorescence; the NO2 group could not be reduced. These compounds were only slightly active or inactive when tested in vitro against Staphylococcus aureus.

Journal of the Chemical Society published new progress about 5738-14-7. 5738-14-7 belongs to pyrimidines, auxiliary class Pyrimidine,Amine,Alcohol,Pyrimidine, name is 2-(Dimethylamino)pyrimidine-4,6-diol, and the molecular formula is C6H9N3O2, Application of 2-(Dimethylamino)pyrimidine-4,6-diol.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia

Sako, Magoichi’s team published research in Journal of Organic Chemistry in 66 | CAS: 608-34-4

Journal of Organic Chemistry published new progress about 608-34-4. 608-34-4 belongs to pyrimidines, auxiliary class Pyrimidine,Amide, name is 3-Methylpyrimidine-2,4(1H,3H)-dione, and the molecular formula is C5H6N2O2, Product Details of C5H6N2O2.

Sako, Magoichi published the artcileReductive Cleavage of Heteroaryl C-Halogen Bonds by Iodotrimethylsilane. Facile and Regioselective Dechlorination of Antibiotic Pyrrolnitrin, Product Details of C5H6N2O2, the publication is Journal of Organic Chemistry (2001), 66(10), 3610-3612, database is CAplus and MEDLINE.

The authors describe regioselective dechlorination of antibiotic pyrrolnitrin (I) via reductive cleavage of heteroaryl C-halogen bonds by iodotrimethylsilane. Reductive cleavage of the C-halo bond proceeds smoothly, efficiently and chemoselectively even under mild conditions with halo uridines and pyrimidines.

Journal of Organic Chemistry published new progress about 608-34-4. 608-34-4 belongs to pyrimidines, auxiliary class Pyrimidine,Amide, name is 3-Methylpyrimidine-2,4(1H,3H)-dione, and the molecular formula is C5H6N2O2, Product Details of C5H6N2O2.

Referemce:
https://pubchem.ncbi.nlm.nih.gov/compound/Pyrimidine,
Pyrimidine – Wikipedia