Tag: 100-200

Action of guanidine and urea on some hydroxymethylene ketones was written by Benayr, Erich. And the article was included in Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen in 1930.Formula: C6H9N3 This article mentions the following:

In general, aliphatic and aliphatic-aromatic hydroxymethylene ketones readily yield the corresponding aminomethylene compounds with primary or secondary organic bases (C. A 24, 4507). In this connection the behavior of MeCOCH:CHOH (I) toward guanidine (II) was also studied. The Na derivative of I reacts with salts of II in alc. at room temperature with formation of 2-amino-4-methylpyrimidine (III), i. e., not only is the HO group replaced by the guanidine residue but ring formation, with further elimination of water, also takes place. The reaction is quite general: analogous products were obtained with the hydroxymethylene derivatives of MeCOEt, MeCOPr, methylheptenone (IV), MeCOPh, MeCOC₆H₄Me and MeCOC₆H₄OMe. The III, now readily available, gives with Br in water a Br derivative (V) in which the Br is held exceedingly firmly and must, therefore, be on the nucleus, probably in position 5. With acid chlorides, however, it readily forms N-derivatives; the ClCH₂CO compound (VI) with hot alc. NH₃ regenerates III in most part while a small part remains unchanged. The pyrimidine formation also takes place with the derivatives of cyclic ketones. Hydroxymethylenecyclohexanone yields Bz-tetrahydro-2-aminoquinazoline (VII) and the hydroxymethylene derivatives of cyclopentanone, menthone and carvone behave in the same way; as these require heat for the reaction and are, in general, more stable than the aliphatic compounds, the desired products are most simply obtained by boiling the free hydroxymethylene compounds with I carbonate in alc. The reaction can be used quite generally to characterize those cyclic ketones which can yield hydroxymethylene derivatives All the bases so obtained do not turn litmus blue and their NH₂ group is held very firmly. The bases can be boiled a long time with dilute HCl without appreciable change and HNO₂ also generally has no action on them. Hydroxymethylenecamphor (VIII) treated as above gives only a trace of quinazoline (IX) which, however, is obtained quite smoothly in boiling AmOH instead of EtOH. Rupe found that with urea VIII splits off only 1 mol. water to form methylenecamphorurea, and B. has now found that ring formation likewise does not occur in the reaction of VIII with CS(NH₂)₂ or of hydroxymethylenecyclohexanone with urea. MeCOC(:CHOH)Me behaves in the same way. The hydroxymethylene ketones, therefore, resemble AcCH₂CO₂Et in their behavior toward urea and II. With hydroxymethyleneacetoacetic ester, II gives iminomethyluracil, resulting from the action of II on AcCH₂CO₂Et, i. e., the HOCH group is split off in the reaction. III is obtained in 51% yield. 5-Br derivative (V), m. 195鎺? N-Chloroacetyl derivative (VI), turns green about 165鎺? then brown and completely decomposes 235鎺? 5-Me derivative, from MeCOC(:CHOH)Me, m. 216-7鎺?(N-chloroacetyl derivative, m. 145-8鎺?. 4-Pr homolog of III, m. 122-3鎺? 4-Ph analog, m. 165鎺? easily soluble in dilute HCl. 4-p-Tolyl homolog, m. 189-91鎺? 4-p-Methoxyphenyl compound, m. 185-7鎺? 4-(4′-Methyl-4′-pentene)-2-aminopyrimidine, from the hydroxymethylene derivative of IV, m. 155-9鎺? VII, m. 206-10鎺? 4,5-Trimethylene-2-aminopyrimidine, from hydroxymethylenecyclopentanone, m. 206-8鎺? 5-Methyl-8-isopropyl-2-aminoquinazoline, m. 139-41鎺? Ac derivative, m. 125-7鎺? 2-Amino-5,6-dihydro-5-isopropenyl-8-methylquinazoline, from hydroxymethylenecarvone, m. 165-7鎺?(13 g. from 45 g. carvone). 2-Aminobornylenepyrimidine (IX) (yield, 55%), m. 249-53鎺? Ac derivative, m. 154-5鎺? chloroacetyl derivative, m. 156-9鎺? Methylenecamphorthiourea, m. 213-4鎺? Methylenecyclohexanoneurea, light yellow, m. 229-30鎺?(decomposition). Methylenemethylethyl ketoneurea, MeCOC(:CHNHCONH₂)Me, m. 156鎺? In the experiment, the researchers used many compounds, for example, 4,5-Dimethylpyrimidin-2-amine (cas: 1193-74-4Formula: C6H9N3).

4,5-Dimethylpyrimidin-2-amine (cas: 1193-74-4) belongs to pyrimidine derivatives. Pyrimidine is an aromatic heterocyclic organic compound similar to pyridine. A Cu-catalyzed and 4-HO-TEMPO-mediated [3 + 3] annulation of commercially available amidines with saturated ketones enables an efficient and facile synthesis of structurally important pyrimidines via a cascade reaction of oxidative dehydrogenation/annulation/oxidative aromatization.Formula: C6H9N3

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

A novel reaction of 6-aminouracils and isatins was written by Dabiri, Minoo;Azimi, Seyyedeh Cobra;Khavasi, Hamid Reza;Bazgir, Ayoob. And the article was included in Tetrahedron in 2008.Product Details of 54030-56-7 This article mentions the following:

A simple and novel cyclocondensation reaction of 6-aminouracils and isatins for the synthesis of spiro[pyrimido[4,5-b]quinoline-5,5′-pyrrolo[2,3-d]pyrimidine] derivatives, e.g., I, is reported. I was subjected to x-ray anal. In the experiment, the researchers used many compounds, for example, 6-Amino-3-methyl-2-(methylthio)pyrimidin-4(3H)-one (cas: 54030-56-7Product Details of 54030-56-7).

6-Amino-3-methyl-2-(methylthio)pyrimidin-4(3H)-one (cas: 54030-56-7) belongs to pyrimidine derivatives. Pyrimidine also found in many synthetic compounds such as barbiturates and the HIV drug, zidovudine. A Cu-catalyzed and 4-HO-TEMPO-mediated [3 + 3] annulation of commercially available amidines with saturated ketones enables an efficient and facile synthesis of structurally important pyrimidines via a cascade reaction of oxidative dehydrogenation/annulation/oxidative aromatization.Product Details of 54030-56-7

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

A facile three-components, one-pot synthesis of pyrimido[4,5-d]pyrimidine-2,5-dione derivatives under microwave-assisted conditions was written by Dabiri, Minoo;Arvin-Nezhad, Hamid;Khavasi, Hamid R.;Bazgir, Ayoob. And the article was included in Journal of Heterocyclic Chemistry in 2007.HPLC of Formula: 54030-56-7 This article mentions the following:

Pyrimido[4,5-d]pyrimidine-2,5-dione derivatives were synthesized in high yields in a novel, 1-pot, and efficient process by condensation of 6-amino-3-methyl-2-(methylthio)pyrimidin-4(3H)-one, aldehydes and urea under microwave-assisted conditions. In the experiment, the researchers used many compounds, for example, 6-Amino-3-methyl-2-(methylthio)pyrimidin-4(3H)-one (cas: 54030-56-7HPLC of Formula: 54030-56-7).

6-Amino-3-methyl-2-(methylthio)pyrimidin-4(3H)-one (cas: 54030-56-7) belongs to pyrimidine derivatives. The pyrimidine ring system has wide occurrence in nature as substituted and ring fused compounds and derivatives. Drugs having the pyrimidine motif have manifested to exhibit gratifying biological activity like anticancer, antiviral, anti-inflammatory, antibacterial, and antihypertensive activities.HPLC of Formula: 54030-56-7

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Structure-based drug design of 1,3,5-triazine and pyrimidine derivatives as novel FGFR3 inhibitors with high selectivity over VEGFR2 was written by Kuriwaki, Ikumi;Kameda, Minoru;Hisamichi, Hiroyuki;Kikuchi, Shigetoshi;Iikubo, Kazuhiko;Kawamoto, Yuichiro;Moritomo, Hiroyuki;Kondoh, Yutaka;Amano, Yasushi;Tateishi, Yukihiro;Echizen, Yuka;Iwai, Yoshinori;Noda, Atsushi;Tomiyama, Hiroshi;Suzuki, Tomoyuki;Hirano, Masaaki. And the article was included in Bioorganic & Medicinal Chemistry in 2020.Reference of 59864-30-1 This article mentions the following:

Fibroblast growth factor receptor 3 (FGFR3) is an attractive therapeutic target for the treatment of bladder cancer. We identified 1,3,5-triazine derivative 18b and pyrimidine derivative 40a as novel structures with potent and highly selective FGFR3 inhibitory activity over vascular endothelial growth factor receptor 2 (VEGFR2) using a structure-based drug design (SBDD) approach. X-ray crystal structure anal. suggests that interactions between 18b and amino acid residues located in the solvent region (Lys476 and Met488), and between 40a and Met529 located in the back pocket of FGFR3 may underlie the potent FGFR3 inhibitory activity and high kinase selectivity over VEGFR2. In the experiment, the researchers used many compounds, for example, 2,6-Dimethoxypyrimidine-4-carboxylic acid (cas: 59864-30-1Reference of 59864-30-1).

2,6-Dimethoxypyrimidine-4-carboxylic acid (cas: 59864-30-1) belongs to pyrimidine derivatives. The pyrimidine nitrogenous bases are derived from the organic compound pyrimidine through the addition of various functional groups. Therapy for fungal infections is based mainly on four classes of antifungals: azoles, echinocandins, polyenes, and pyrimidine analogs.Reference of 59864-30-1

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Reactivity of pyrimidinylphosphazenes with acetylenic esters: Competitive [4 + 2] and [2 + 2] tandem cycloaddition or retro-cycloaddition approaches was written by Cobo, Justo;Molina, Sebastian;Sanchez, Adolfo;Nogueras, Manuel;Insuasty, Braulio;Orozco-Lopez, Fabian. And the article was included in Journal of Heterocyclic Chemistry in 2022.Related Products of 54030-56-7 This article mentions the following:

In the search for new intermediates for heterocyclic synthesis, the reactivity of 6-iminophosphoranepyrimidines against di-Me acetylenedicarboxylate (DMAD) and Et propiolate as dienophiles, was studied. The presence of a viable 2-azadienic moiety in pyrimidin-4-one rings (oxo derivatives) favored reaction of DMAD by [4 + 2]/retro-[4 + 2] sequence, in addition to the expected [2 + 2] cycloaddition/retrocycloaddn. involving phosphazene moiety. In contrast, pyrimidine derivatives lacking a viable 2-azadienic residue reacted only through phosphazene group by the aforementioned [2 + 2]/retro-[2 + 2] tandem process. Et propiolate (nonsym. dienophile) proved less reactive giving rise to undesired side reactions. In the experiment, the researchers used many compounds, for example, 6-Amino-3-methyl-2-(methylthio)pyrimidin-4(3H)-one (cas: 54030-56-7Related Products of 54030-56-7).

6-Amino-3-methyl-2-(methylthio)pyrimidin-4(3H)-one (cas: 54030-56-7) belongs to pyrimidine derivatives. Pyrimidine is an aromatic heterocyclic organic compound similar to pyridine. As nucleotides in DNA and RNA, pyrimidine nucleotide derivatives have a wide range of biological applications. For example, pyrimidine derivatives are useful in DNA repair studies involving cancer and epigenetics.Related Products of 54030-56-7

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthesis and bioevaluation of diaryl urea derivatives as potential antitumor agents for the treatment of human colorectal cancer was written by Wu, Chun-Feng;Wang, Qing-Chen;Chen, Rui;Zhou, Hai-Ling;Wu, Ting-Ting;Du, Yao;Zhang, Na-Na;Zhang, Hui-Min;Fan, Zu-Yan;Wang, Li-Li;Hu, Chu-Jiao;Sang, Zhi-Pei;Li, Hong-Liang;Wang, Ling;Tang, Lei;Zhang, Ji-Quan. And the article was included in European Journal of Medicinal Chemistry in 2022.Category: pyrimidines This article mentions the following:

The development of inhibitors targeting the PI3K-Akt-mTOR signaling pathway has been greatly hindered by the on-target AEs, such as hyperglycemia and hepatotoxicities. In this study, a series of diaryl urea derivatives has been designed and synthesized based on clin. candidate gedatolisib, and most of the newly synthesized derivatives showed kinase inhibitory and antiproliferative activities within nanomolar and submicromolar level, resp. The terminal L-proline amide substituted derivative I showed 8.6-fold more potent PI3K浼?inhibitory activity (0.7 nM) and 4.6-fold more potent antiproliferative effect against HCT116 cell lines (0.11娓璏) compared with control gedatolisib. The potential antitumor mechanism and efficacy of I in HCT116 xenograft models have also been evaluated, and found I showed comparable in vivo antitumor activity with gedatolisib. The safety investigations revealed that compound I exhibited more safer profiles in the selectivity of liver cells (selectivity index: >6.6 vs 1.85) and blood glucose regulation than gedatolisib. In addition, the in vitro stability assays also indicated that developed compound I possessed good metabolic stabilities. In the experiment, the researchers used many compounds, for example, 4-(2-Chloropyrimidin-4-yl)morpholine (cas: 62968-37-0Category: pyrimidines).

4-(2-Chloropyrimidin-4-yl)morpholine (cas: 62968-37-0) belongs to pyrimidine derivatives. The pyrimidine derivatives can easily interact with enzymes, genetic materials, and bio components within the cell. Therapy for fungal infections is based mainly on four classes of antifungals: azoles, echinocandins, polyenes, and pyrimidine analogs.Category: pyrimidines

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthesis and herbicidal activity of 2-benzoyliminopyrimido[3,2-b]-1,2,4-thiadiazolines was written by Xue, Si Jia;Tan, Dong Yun;Sun, Chang You. And the article was included in Chinese Chemical Letters in 1998.Category: pyrimidines This article mentions the following:

The title compounds, i.e., N-([1,2,4]thiadiazolo[2,3-a]pyrimidinylidene)benzamides [2-benzoyliminopyrimido[3,2-b]-1,2,4-thiadiazolines], were synthesized and tested for herbicidal effects. All of them are new compounds and their structures were confirmed by ¹HNMR, IR, MS. The preliminary herbicidal tests show that some of the target compounds have potent activity and very good selectivity to rice. Of the target compounds thus prepared and tested was N-(6,7-Dimethoxy-2H-[1,2,4]thiadiazolo[2,3-a]pyrimidin-2-ylidene)benzamide. In the experiment, the researchers used many compounds, for example, 4,5-Dimethylpyrimidin-2-amine (cas: 1193-74-4Category: pyrimidines).

4,5-Dimethylpyrimidin-2-amine (cas: 1193-74-4) belongs to pyrimidine derivatives. Pyrimidine is an aromatic heterocyclic organic compound similar to pyridine. Pyrimidine derivatives have been used in a wide variety of pharmaceuticals including general anesthetics, anti-epilepsy medication, anti-malaria medication, drugs for treating high blood pressure, and HIV medication.Category: pyrimidines

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Proton and carbon-13 nuclear magnetic resonance studies of substituted pyrimidines. 2. Monoprotonation of methyl- and aminopyrimidines was written by Riand, J.;Chenon, M. T.;Lumbroso-Bader, N.. And the article was included in Journal of the American Chemical Society in 1977.Category: pyrimidines This article mentions the following:

The monoprotonation of methyl- and aminopyrimidines was studied by C13 NMR spectroscopy. The chem.-shift parameters associated with the protonation of methylpyrimidines were determined for the aromatic and Me group C atoms from the salts of certain sym. compounds A significant difference exists for certain parameters for a given C, depending on whether a H atom or a Me group is attached to it. An especially large solvent effect exists for C atoms bearing a Me group para to the site of protonation. The percentages of the forms monoprotonated at sites N-1 or N-3 of pyrimidines were evaluated from their chem. shifts in F3CCO2H and Me2SO. For methylpyrimidines a higher percentage (闂?1%) of the form in which the protonated N is in the para position to the Me group is found. For the 4-amino-6-methylpyrimidines, the influence of the amino group is greater than that of the Me group, and the percentage reaches 闂?4% for the form in which the protonated N is in the para position to the amino group. In the experiment, the researchers used many compounds, for example, 4,5-Dimethylpyrimidin-2-amine (cas: 1193-74-4Category: pyrimidines).

4,5-Dimethylpyrimidin-2-amine (cas: 1193-74-4) belongs to pyrimidine derivatives. Pyrimidine also found in many synthetic compounds such as barbiturates and the HIV drug, zidovudine. Drugs having the pyrimidine motif have manifested to exhibit gratifying biological activity like anticancer, antiviral, anti-inflammatory, antibacterial, and antihypertensive activities.Category: pyrimidines

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Synthesis of novel pyrimido[4,5-b]quinolin-4-ones with potential antitumor activity was written by Insuasty, Braulio;Becerra, Diana;Quiroga, Jairo;Abonia, Rodrigo;Nogueras, Manuel;Cobo, Justo. And the article was included in Journal of Heterocyclic Chemistry in 2013.Recommanded Product: 54030-56-7 This article mentions the following:

5,6,7,8,9,10-Hexahydro-2-(methylthio)pyrimido[4,5-b]quinolines and their oxidized forms, the corresponding 6,7,8,9-tetrahydropyrimido[4,5-b]quinolin-4(3H)-ones, were obtained from the reaction of 6-amino-2-(methylthio)pyrimidin-4(3H)-one or its 3-Me derivative and 濞?閻?unsaturated ketones using BF₃.OEt₂ as catalyst and 4-chloranil as oxidizing agent. Some of the new compounds were evaluated in the US National Cancer Institute (NCI), where (9E)-9-benzylidene-3-methyl-2-(methylthio)-5-phenyl-5,6,7,8,9,10-hexahydropyrimido[4,5-b]quinolin-4(3H)-one presented remarkable activity against cancer cell lines, with the most important GI₅₀ values of 0.72-18.4 婵炴挾鎷?from in vitro assays. In the experiment, the researchers used many compounds, for example, 6-Amino-3-methyl-2-(methylthio)pyrimidin-4(3H)-one (cas: 54030-56-7Recommanded Product: 54030-56-7).

6-Amino-3-methyl-2-(methylthio)pyrimidin-4(3H)-one (cas: 54030-56-7) belongs to pyrimidine derivatives. The aromatic compound pyrimidine, and its derivatives, are ubiquitous in nature. They are found in nucleic acids, vitamins, amino acids, antibiotics, alkaloids, and a variety of toxins. Pyrimidine derivatives also play an important role in drug development, either in concert with other compounds or on their own.Recommanded Product: 54030-56-7

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Investigation in the pyrimidine series V. Acylation of 6-amino-4-oxodihydropyrimidines was written by Pfleiderer, Wolfgang;Liedek, Egon. And the article was included in Justus Liebigs Annalen der Chemie in 1957.Synthetic Route of C6H9N3OS This article mentions the following:

Acylation in the 6-amino-4-oxodihydropyrimidine system occurred in normal fashion on the amino group, as determined by synthesis and by ultraviolet spectral data. NH.CS.NH.CO.CH:CNH₂ (I) (14.3 g.) dissolved in 140 cc. H₂O and 14 cc. concentrated NH₄OH by warming, 42 g. Raney Ni added portionwise at 80鎺? the mixture refluxed 3 hrs., filtered hot, the filtrate kept several hrs. in the refrigerator, the precipitate (II) filtered off, the filtrate concentrated to furnish a 2nd fraction (III), and II and III combined and recrystallized from H₂O gave 6.7 g. N:CH.NH.CO.CH:CNH₂ (IV), m. 271-2鎺?(decomposition). IV (5 g.) and 50 cc. Ac₂ refluxed 30 min., cooled, and the precipitate collected (addnl. material by concentrating the filtrate) and recrystallized from H₂O gave 5.4 g. 6-AcNH analog (V), m. 288-9鎺? I (57 g.) in 600 cc. 2N NaOH treated slowly at 40鎺?with 150 cc. Me₂SO₄ with stirring (a pH of 9 maintained toward the end of the methylation), the precipitate filtered off after 6 hrs., dried, digested with Et₂O, filtered off, and recrystallized from H₂O gave 48 g. N:C(SMe).NMe.CO.CH:CNH₂ (VI), m. 257鎺? VI (17.1 g.) and 120 cc. Ac₂O refluxed 30 min., cooled, the precipitate collected, and recrystallized from aqueous EtOH gave 9.2 g. 6-AcNH analog (VII), m. 251鎺? To 17.1 g. VI in 400 cc. H₂O was added 17.1 g. Raney Ni at 80鎺? refluxed 3.5 hrs., filtered hot, the filtrate concentrated to 1/3 its volume, the concentrate kept several hrs. in the refrigerator, the precipitate filtered off, and recrystallized from H₂O to give 6.5 g. N:CH.NMe.CO.CH:CNH₂ (VIII), m. 184-5鎺? III (3.7 g.) in 25 cc. 2N NaOH treated dropwise at 40鎺?with 5 cc. Me₂SO₄ with stirring while maintaining a pH of 9 at all times, the mixture neutralized with AcOH, extracted continuously 8 hrs. with CHCl₃, the extract dried, evaporated, and the residue recrystallized from H₂O gave 1.3 g. VIII. V (3.8 g.) in 40 cc. N NaOH treated as above with 4 cc. Me₂SO₄ gave 2.1 g. N:CH.NMe.CO.CH:CNHAc (IX), m. 303-4鎺? VIII (4.1 g.) and 20 cc. Ac₂O refluxed 15 min., cooled, the precipitate filtered off, and crystallized from H₂O gave 3 g. IX. VII (7.1 g.) in 200 cc. H₂O treated portionwise with 50 g. Raney Ni, refluxed 4 hrs., filtered hot, the filtrate concentrated to 1/3 its volume, cooled, the precipitate collected, and crystallized from H₂O gave 4.5 g. IX. N:CS.NH.CO.CMe:CNH₂ (15.7 g.) in 200 cc. H₂O treated with 45 g. Raney Ni, refluxed 4 hrs., filtered hot, the filtrate cooled several hrs. in ice, and the precipitate crystallized from H₂O gave 10 g. N:CH.NH.CO.CMe:CNH₂ (X), m. 243鎺? X (3.1 g.) and 9 cc. Ac₂O refluxed 15 min., cooled, and the precipitate recrystallized from H₂O gave 2 g. 6-AcNH analog, m. 303鎺? In the experiment, the researchers used many compounds, for example, 6-Amino-3-methyl-2-(methylthio)pyrimidin-4(3H)-one (cas: 54030-56-7Synthetic Route of C6H9N3OS).

6-Amino-3-methyl-2-(methylthio)pyrimidin-4(3H)-one (cas: 54030-56-7) belongs to pyrimidine derivatives. Pyrimidine also found in many synthetic compounds such as barbiturates and the HIV drug, zidovudine. Pyrimidine derivatives have been used in a wide variety of pharmaceuticals including general anesthetics, anti-epilepsy medication, anti-malaria medication, drugs for treating high blood pressure, and HIV medication.Synthetic Route of C6H9N3OS

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia