Abstract
Condensation of 2-ethyl-4-amino-5-aminomethylpyrimidine (VI) with γ-aceto-γ-chloropropyl acetate (IV) or its alcohol (X), in the presence of carbon disulfide and ammonia, respectively yields α-aceto-γ-acetoxypropyl N-[2-ethyl-4-aminopyrimidyl (5)]-methyldithiocarbamate (VII) or α-aceto-γ-hydroxypropyl N-[2-ethyl-4-aminopyrimidyl (5)]-methyldithiocarbamate (XI). Both (VIII) and (XI) give 3-[2′-ethyl-4′-aminopyrimidyl (5′)]-methyl-4-methyl-5-β-hydroxyethylthiothiazolone (2) (VIII) by heating their respective solution in diluted hydrochloric acid. Heating their respcetive caustic alkali solution or heating their crystals to above their decomposition points results in the formation of 2-thio-7-ethyl-1, 2, 3, 4-tetrahydropyrimido-(4·5-d)-pyrimidine (IX). Oxidation of (VIII) with hydrogen peroxide in acid medium, followed by treatment with barium chloride gives, with a good yield, 3-[2′-ethyl-4′-aminopyrimidyl (5′)]-methyl-4-methyl-5-β-hydroxyethylthiazolium chloride hydrochloride (XVIII). Acetylation of (VIII) with acetic anhydride an pyridine yields 3-[2′-ethyl-4′-aminopyrimidyl (5′)]-methyl-4-methyl-5-β-acetoxyethylthiothiazolone (2). Use of 2-benzyl-4-amino-5-aminomethylpyrimidine (XII) in place of 2-ethyl-4-amino-5-aminomethylpyrimidine (VI) allows similar reactions to proceed.
