Category: 15837-41-9

Ferris, J. P.; Joshi, P. C.; Lawless, J. G. published the artcile< Chemical evolution. XXIX. Pyrimidines from hydrogen cyanide>, Related Products of 15837-41-9, the main research area is pyrimidine formation prebiosis; hydrogen cyanide pyrimidine formation.

Dilute (0.1M) solutions of HCN condensed to oligomers at pH 8-9. Hydrolysis of these oligomers at pH 8.5 or with 6N HCl yielded 4,5-dihydroxypyrimidine as the most abundant pyrimidine product along with orotic acid and 5-hydroxyuracil. Thus, the 3 major N-containing classes of biomols. could have originated from HCN on the primitive earth. The observation of the formation of orotic acid and 4-aminoimidazole-5-carboxamide by the hydrolysis of the HCN oligomers suggested that once the initially formed pyrimidines and purines were consumed, those life forms persisted which evolved enzymes for the conversion of these intermediates to the pyrimidines and purines present in contemporary RNA.

BioSystems published new progress about Molecular evolution. 15837-41-9 belongs to class pyrimidines, and the molecular formula is C4H4N2O2, Related Products of 15837-41-9.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

O’Brien, Darrell E.; Weinstock, Louis T.; Springer, Robert H.; Cheng, Chia-Chung published the artcile< Pyrimidines. XIX. Pyrimidol[4,5 - e]dihydro - 1,3-oxazines and related compounds>, Category: pyrimidines, the main research area is PYRIMIDO DIHYDRO OXAZINES; OXAZINES PYRIMIDO DIHYDRO.

A number of 2-substituted 4,5-dihydroxy-6-(substituted aminomethyl)pyridimines (I) were prepared from the corresponding 2-substituted 4,5-dihydroxypyrimidines by a new pyrimidine Mannich reaction. The structure of I was proved by an independent synthesis. Further study of this reaction led to the synthesis of pyrimido[4,5-e]dihydro-1,3-oxazines (II). 24 references.

Journal of Heterocyclic Chemistry published new progress about Mannich reaction. 15837-41-9 belongs to class pyrimidines, and the molecular formula is C4H4N2O2, Category: pyrimidines.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Ferris, J. P.; Joshi, P. C.; Edelson, E. H.; Lawless, J. G. published the artcile< Chemical evolution. XXX. Hydrogen cyanide: a plausible source of purines, pyrimidines and amino acids on the primitive earth>, Recommanded Product: 5-Hydroxypyrimidin-4(3H)-one, the main research area is hydrocyanate chem evolution; amino acid formation hydrocyanate prebiotic; pyrimidine formation hydrocyanate prebiotic; purine formation hydrocyanate prebiotic.

Dilute (0.1M) solutions of HCN condense to oligomers at pH 9.2. Hydrolysis of these oligomers yields 4,5-dihydroxypyrimidine, orotic acid, 5-hydroxyuracil, adenine, 4-aminoimidazole-5-carboxamide, and amino acids. These results, together with the earlier data, demonstrate that the 3 main classes of N-containing biomols., purines, pyrimidines, and amino acids may have originated from HCN on the primitive earth. The observation of orotic acid and 4-aminoimidazole-5-carboxamide suggests that the contemporary biosynthetic pathways for nucleotides may have evolved from the compounds released on hydrolysis of HCN oligomers.

Journal of Molecular Evolution published new progress about Amino acids Role: BSU (Biological Study, Unclassified), BIOL (Biological Study). 15837-41-9 belongs to class pyrimidines, and the molecular formula is C4H4N2O2, Recommanded Product: 5-Hydroxypyrimidin-4(3H)-one.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Miyakawa, Shin; Yamanashi, Hiroto; Kobayashi, Kensei; Cleaves, H. James; Miller, Stanley L. published the artcile< Prebiotic synthesis from CO atmospheres: implications for the origins of life>, Related Products of 15837-41-9, the main research area is carbon monoxide primordial atm prebiotic amino acid life origin.

Most models of the primitive atm. around the time life originated suggest that the atm. was dominated by carbon dioxide, largely based on the notion that the atm. was derived via volcanic outgassing, and that those gases were similar to those found in modern volcanic effluent. These models tend to downplay the possibility of a strongly reducing atm., which had been thought to be important for prebiotic synthesis and thus the origin of life. However, there is no definitive geol. evidence for the oxidation state of the early atm. and bioorganic compounds are not efficiently synthesized from CO2 atmospheres. In the present study, proton-beam irradiation of equimol. mixtures of CO and N2 in the presence of water induced abiotic synthesis of uracil, orotic acid, 5-hydroxyuracil, nicotinic acid, and 4,5-dihydroxypyrimidine. This and similar previous observations suggest that a CO-CO2-N2-H2O atm. can give a variety of bioorganic compounds with yields comparable to those obtained from a strongly reducing atm. Atmospheres containing carbon monoxide might therefore have been conducive to prebiotic synthesis and perhaps the origin of life. CO-dominant atmospheres could have existed if the production rate of CO from impacts of extraterrestrial materials were high or if the upper mantle had been more reduced than today.

Proceedings of the National Academy of Sciences of the United States of America published new progress about Life, origin. 15837-41-9 belongs to class pyrimidines, and the molecular formula is C4H4N2O2, Related Products of 15837-41-9.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

O’Brien, Darrell E.; Springer, Robert H.; Cheng, C. C. published the artcile< New Mannich reaction of pyrimidines>, Safety of 5-Hydroxypyrimidin-4(3H)-one, the main research area is .

4,5-Dihydroxypyrimidines undergo the Mannich reaction with primary and secondary amines and CH2O at the 6-position. 5-Hydroxy-6-piperidinomethyluracil, 3,6-dimethyl-3,4-dihydro-2H-pyrimido[4,5-e]-1,3-oxazin-8-ol (I, R = Me), and the 6-OH analog of I were prepared in this manner. The new Mannich reaction appears to be a general method for the synthesis of compounds containing the new 3,4-dihydro-2H-pyrimido[4,5-e]-1,3-oxazine ring system.

Journal of Heterocyclic Chemistry published new progress about Mannich reaction. 15837-41-9 belongs to class pyrimidines, and the molecular formula is C4H4N2O2, Safety of 5-Hydroxypyrimidin-4(3H)-one.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Cleaves, H. James II published the artcile< The Reactions of Nitrogen Heterocycles with Acrolein: Scope and Prebiotic Significance>, Name: 5-Hydroxypyrimidin-4(3H)-one, the main research area is acrolein nucleobase adduct Michael addition prebiotic evolution.

It was suggested that life began with a self-replicating RNA mol. However, after much research into the prebiotic synthesis of RNA, the difficulties encountered have lead some to hypothesize that RNA was preceded by a simpler mol., 1 more easily synthesized prebiotically. Many of the proposed alternative mols. are based on acrolein, since it reacts readily with nucleophiles, such as the nucleobases, via Michael addition and is readily synthesized from formaldehyde and acetaldehyde. Reports regarding the reactions of nucleobases with concentrated acrolein solutions suggest that this is a plausible reaction mechanism, though there are also reports that the “”incorrect”” isomers are obtained. The scope and kinetics of the reaction of acrolein with various nitrogen heterocycles are reported here. Reactions of pyrimidines often give N1 adducts as the major products. Reactions of purines often give N9 adducts in good yield. The reactions are rapid under neutral to slightly alk. conditions, and proceed at low temperatures and dilutions The implications of these findings for the origin of life are discussed.

Astrobiology published new progress about Addition compounds. 15837-41-9 belongs to class pyrimidines, and the molecular formula is C4H4N2O2, Name: 5-Hydroxypyrimidin-4(3H)-one.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Sodum, Rama S.; Klein, Robert S.; Otter, Brian A. published the artcile< Chemistry of 4-pyrimidinones: acetylation and ring-opening reactions>, Name: 5-Hydroxypyrimidin-4(3H)-one, the main research area is pyrimidinone acetylation ring cleavage.

4(3H)-Pyrimidinone (I), as well as its 5-acetoxy and 5-methoxy derivatives, undergoes selective acetylation at N-1 when treated with acetic anhydride. In the presence of water, these 1-acetylpyrimidines undergo spontaneous covalent hydration at C-2 and cleavage of the 1,2-bond to give crystalline cis-3-acetylamino-N-formylacrylamides, generally in good yield. In contrast, the 6-Me derivative of 4(3H)-pyrimidinone forms an equilibrium mixture of acetylated products that undergo the ring opening process to only a very limited extent, the major product (11%) being 3-formylamino-N-acetylacrylamide derivative formed via N-3 acetylation and cleavage of the 2,3-bond.

Journal of Heterocyclic Chemistry published new progress about Acetylation. 15837-41-9 belongs to class pyrimidines, and the molecular formula is C4H4N2O2, Name: 5-Hydroxypyrimidin-4(3H)-one.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Ta-Shma, Rachel; Torres, Avital; Chevion, Mordechai; Breuer, Eli; Quntar, Abed Al Aziz; Enk, Claes D.; Srebnik, Morris published the artcile< An autoxidation study of C2 substituted pyrimidine amino reductones>, Safety of 5-Hydroxypyrimidin-4(3H)-one, the main research area is autoxidation pyrimidine amino reductone.

Three pyrimidine derivatives I (R = Me, H, SMe) , differing from isouramil(I; R = OH) and divicine (I; R = NH2) at C2, were synthesized and their autoxidation rates measured spectrophotometrically. The autoxidation rates of all five pyrimidines were correlated with σ p + values (rho = -1.28, r2 = 0.949).

Tetrahedron published new progress about Autoxidation. 15837-41-9 belongs to class pyrimidines, and the molecular formula is C4H4N2O2, Safety of 5-Hydroxypyrimidin-4(3H)-one.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Miyakawa, Shin; Cleaves, H. James; Miller, Stanley L. published the artcile< The Cold Origin of Life: B. Implications Based on Pyrimidines and Purines Produced From Frozen Ammonium Cyanide Solutions>, Application In Synthesis of 15837-41-9, the main research area is ammonium cyanide purine pyrimidine life origin.

A wide variety of pyrimidines and purines were identified as products of a dilute frozen ammonium cyanide solution that had been held at -78° for 27 yr. This demonstrates that both pyrimidines and purines could have been produced on the primitive earth in a short time by eutectic concentration of HCN, even though the concentration of HCN in the primitive ocean may have been low. We suggest that eutectic freezing is the most plausible demonstrated mechanism by which HCN polymerizations could have produced biol. important prebiotic compounds

Origins of Life and Evolution of the Biosphere published new progress about Freezing (eutectic). 15837-41-9 belongs to class pyrimidines, and the molecular formula is C4H4N2O2, Application In Synthesis of 15837-41-9.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia

Chang, P.; Chiang, Kwei-Che published the artcile< 5-Hydroxypyrimidines. II. Synthesis of 2-substituted 4,5-dihydroxypyrimidines>, Recommanded Product: 5-Hydroxypyrimidin-4(3H)-one, the main research area is .

V reacts with HCO2Et gives PhCH2OCH(CHO)CO2Et (X), which condenses with various amidines [RC(:NH)NH2] to 2-R-substituted-5-benzyloxy-4-hydroxypyridines (XI, R), converted by H in the presence of Pd to XII(R). [N:CR.N:C(OH).C(OCH2Ph):CH (XI) and N:CR.N:C(OH).C(OH):CH (XII) are designated by the Roman numeral, followed by R.] XI and XII are stable, high-melting solids, the latter giving the same pos. color tests as III (except that the FeCl3-NH3 colors are different), and reducing 2,6-dichlorophenolindophenol rapidly. When a suspension of NaOMe (from 2.8 g. powd. Na and 10 ml. anhydrous MeOH in 100 ml. dry Et2O) is treated with a 20 g. V and 14 g. HCO2Et with stirring at room temperature during 2 hrs., and stirred 4 hrs. more, the mixture turns from light to orange yellow and a white amorphous solid seps.; after 2 days, 40 ml. H2O, then 12 ml. dilute HOAc are added, the Et2O layer is dried, distilled, and the fraction b1 110-33° or b4 140-53° redistilled, giving 79% X, b1 128-30°, b4 149°, n20D 1.5200, which turns blue-violet with FeCl3. No X is obtained with powd. Na used directly, and solutions of Na in MeOH or EtOH give only 15-20% X. Urea (1.2 g.) added to 0.92 g. Na in 30 ml. anhydrous EtOH, 4.5 g. X stirred in during 1 hr. at room temperature, the mixture heated 4 hrs. on steam, cooled, the solids dissolved by addition of H2O, and the mixture acidified with 6 ml. HOAc gives 70% XI(OH), m. 283° (20% aqueous HOAc)(decomposition). X and IX at room temperature give 78% XI(NH2), m. 243° (20% aqueous HOAc) (decomposition); X and MeC(:NH)NH2.HCl (at 60°) give 93% XI(Me), fine needles from H2O, m. 186°; and NH2CSNH2 [or NH2C(:NH)SEt.HBr, loss of Et occurring during the condensation] and X (at room temperature) give 92% XI(SH), long needles from EtOH, m. 225-6° (decomposition). XI(SEt), m. 189-90°, is obtained by adding 2 ml. EtBr to 0.5 g. XI(SH) in 15 ml. 10% NaOH, heating 3 hrs. on steam, cooling, acidifying with dilute HCl, and recrystallizing the precipitate from EtOH, yield 53.6%. Boiling XI(SH or SEt) in dilute NH4OH with Raney Ni yields XI(H) [83% from XI(SH)], needles, m. 98-9°. Hydrogenation of XI(OH) (0.5 g.) in 30 ml. 5% NaOH containing Pd at room temperature and atm. pressure required 30 min.; acidification of the filtered mixture precipitated XII(OH) (isobarbituric acid), m. 310° (decomposition) (from H2O), yield quant.; addition of XII(OH) to 5% AgNO3 results in immediate precipitation of black metallic Ag. Hydrogenation of XI(NH2) (in HCO2H) gives a quant. yield of XII(NH2) unmelted at 340°. Similarly, XI(Me) is converted to XII(Me), m. 312-13° (decomposition), and XI(H) is reduced to XII(H), m. 268-9° (decomposition). While XII(OH) (like III) gives a blue-violet color on treatment with 1% FeCl3 and a few drops of concentrated NH4OH, XII (R = NH2, H, and Me) give brown colors.

Scientia Sinica (English Edition) published new progress about Color reaction. 15837-41-9 belongs to class pyrimidines, and the molecular formula is C4H4N2O2, Recommanded Product: 5-Hydroxypyrimidin-4(3H)-one.

Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia