スルファニルアミド誘導体の合成研究 (第2報)

メトキシピリミジン類の液体アンモニア中ナトリウムアミドによる置換反応とN¹-(6-メトキシ-4-ピリミジニル) スルファニルアミドの合成

抄録

The substitution reaction of pyrimidine derivatives having methoxyl groups with sodium amide in liquid ammonia are described. That is, 2-amino-4-methoxy-6-pyrimidinethiol (II) (50%) and 2-amino-4, 6-dimethoxypyrimidine (III) (1.6%) from 2, 4-dimethoxy-6-pyrimidine thiol (I), 2-amino-4-methoxy-6-methylthiopyrimidine (V) (50%) from 6-methylthio-2, 4-dimethoxypyrimidine (IV) which was produced by the methylation of (I), 2-amino-4-methoxypyrimidine (VII) (65%) and 2-methoxy-4-amino-pyrimidine (VIII) (10.4%) from 2, 4-dimethoxypyrimidine (VI), 2-aminopyrimidine (X) (19%) from 2-methoxypyrimidine (IX), and finally 4-amino-6-methoxypyrimidine (XII) (85%) from 4, 6-dimethoxypyrimidine (IX) were synthesized. In addition, the condensation between (XII) and N-acetylsulfanilylchloride gave N¹-(6-methoxy-4-pyrimidyl)-N⁴-acetylsulfanilamide (XIII), followed by the hydrolysis to N¹-(6-methoxy-4-pyrimidyl)-sulfanilamide, being approved to be superior sulfa drug.