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
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