含硫黄ピリミジン誘導体の研究 (第2報)

イソチオ尿素誘導体の合成

抄録

Several kinds of thiourea derivatives were condensed with 2-methyl-4-amino-5-chioromethylpyrimidine hydrochloride (I) to form isothiuronium salts (II) and their properties were compared. Compounds of the formula (II), where R is phenyl, benzyl, methyl, or amino, change to bis (2-methyl-4-amino-5-pyrimidylmethyl) sulfide (XI) (cf. Table I) when aqueous solution of (II) obtained on neutralization with sodium hydrogen carbonate is heated. Hydrogen peroxide oxidation of alkaline solution of (II) affords his (2-methyl-4-amino-5-pyrimidylmethyl) disulfide (XII). On heating hydrochloric acid solution of (II), compounds with phenyl or methyl undergo cyclization to form 7-methyl-4H-pyrimido [4, 5-d]-m-thiazin-2 (1H)-one (XIII) while those with benzyl and amino do not form the thiazine ring but undergo hydrolysis of the imino group to the carbonyl to form the compounds (XIV) and (XV).