Some thiopyrimidine derivatives was written by Monti, Lydia;Pacini, Carlo. And the article was included in Gazzetta Chimica Italiana in 1948.Product Details of 39083-15-3 The following contents are mentioned in the article:
By the reaction of HCHO (I), in the presence of H2SO4, on thiopyrimidines of the HN.CO.CH:CR.NH.CS ⇄ N:C(OH).CH:CR.N:CSH (II) and HN.CO.CR’:CMe.NH.CS ⇄ N:C(OH).CR’:CMe.N:CSH (III) types, 2 series of new derivatives were obtained. They are essentially different from those prepared by Kircher (C.A. 6, 857) and Poetsch and Behrend (C.A. 20, 2681) by the action of I on HN.CO.CH:CMe.NH.CO and HN.CO.CH:CMe.NH.CS, resp., in acid medium. With II the reactions involve the initial reaction of I with enolic II in the 5-position, following which another I mol. reacts with the newly formed OH group and the original OH group in the 6-position, with final formation of compounds of the C:CR.N:C(SH).N:C.O.CH2.O.CH2 (IV) type. With III, in which the H in the 5-position is replaced by an alkyl group, the formation of analogous compounds is difficult to explain, for no intermediate products could be isolated. Perhaps I reacts with III in the ketone-imide form with formation of SC.N.CO.CR’:CMe.N.CH2.O.CH2 compounds If so, 1,3-dimethylol compounds would be intermediate products, but none was isolated. Possibly the NH group in the 1-position (between CS and CO) is more reactive than that in the 3-position, and SC.N.CH2.O.CH2.O.C:CR’.CMe:N or S.CH2.O.CH2.N.CO.CR’:CMe.N:C compounds are formed. Or III compounds may react in a tautomeric form N:C(OH).CHR’.CMe:N.CS, with formation of N:C.O.CH2.O.CH2.CR’.CMe:N.CS compounds Comparative physiol. tests of these doubtful compounds and of II, III, and IV now in progress may help solve this problem. (H2N)2CS (2.5 g.), 6 g. AcAmCHCO2Et, and alc. NaOEt (from 1.5 g. Na in a min. of EtOH), refluxed 30-40 min., evaporated, the residue taken up in AcOH (60 cc. AcOH + 40 cc. water), filtered, and the product purified by water, yield 60% of 4-methyl-5-amyl-2-thiouracil (V), m. 217-19°, soluble in dilute aqueous alkalies, and decomposed by boiling concentrated aqueous alkalies (evolution of H2S and NH3). It behaves like a weak monobasic acid. With aqueous AgNO3, its boiling concentrated aqueous solutions deposit the Ag salt, C10H15ON2SAg. The Cu and Hg salts were prepared similarly. 4-Phenyl-2-thiouracil (IV) (2 g.) in 15 cc. hot 10% aqueous NaOH, allowed to stand 24 hrs. with 4 cc. 40% I, diluted, neutralized with dilute HCl, and the precipitate purified by EtOH, yields 86% 5-(hydroxymethyl)-4-phenyl-2-thiouracil (VII), m. 250-1°, evolves I when heated; its solutions in concentrated H2SO4 are intensely yellow. 4-Methyl-2-thiouracil (2 g.), 16 cc. dilute H2SO4 (4 volumes concentrated H2SO4 + 1 volume water), and 3 cc. 40% I, allowed to stand 24 hrs. (with frequent agitation), diluted with 100 cc. water, neutralized with NH4OH, filtered, and the residue purified by boiling water and CCl4, yield the methylenic ether of 2-thio-4-methyl-6-hydroxy-5-pyrimidinemethanol (VIII), does not form an Ac derivative; its concentrated H2SO4 solution with a trace of gallic acid gives the green-to-blue Labat reaction; when heated with a dilute alkali, it evolves H2S and NH3. VII and I in dilute H2SO4, also under the same conditions, form VIII. VI or VII (3 g.) and 4 cc. 40% I in 16 cc. dilute H2SO4 (4 volumes concentrated H2SO4 + 1 volume water), treated as above, yield 95% of methylenic ether of 2-thio-4-phenyl-6-hydroxy-5-pyrimidinemethanol, m. 151-2°, yellow when crystallized from EtOH but colorless from CCl4. It gives a pos. Labat reaction, and is decomposed, with evolution of H2S and NH3, by hot dilute alkalies. Prepared under similar conditions from 4,5-dimethyl-2-thiouracil (IX) and I in 73% yield and purified by boiling water, the methylenic ether (X) of IX m. 133-5°, does not give an Ac derivative, gives a pos. Labat reaction, and is decomposed by hot aqueous alkalies with evolution of H2S and NH3. 4-Methyl-5-ethyl-2-thiouracil and I give 82-3% of the methylenic ether (XI), m. 163-4°, with chem. properties similar to those of X. V (2 g.) in 22 cc. dilute H2SO4 (same concentration as before) and 3 cc. 40% I, allowed to stand 24 hrs., diluted, neutralized with NH4OH, concentrated, and the product purified by boiling water, yield 41% of the methylenic ether, m. 122-5°, with chem. properties like those of X and XI. This study involved multiple reactions and reactants, such as 5-Ethyl-6-methyl-2-thioxo-2,3-dihydropyrimidin-4(1H)-one (cas: 39083-15-3Product Details of 39083-15-3).
5-Ethyl-6-methyl-2-thioxo-2,3-dihydropyrimidin-4(1H)-one (cas: 39083-15-3) belongs to pyrimidine derivatives. The pyrimidine derivatives can easily interact with enzymes, genetic materials, and bio components within the cell. Pyrimidine derivatives also play an important role in drug development, either in concert with other compounds or on their own.Product Details of 39083-15-3
Referemce:
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia