Pyrimidine Derivatives and Related Compounds. XIV. The Synthesis of N-Substituted Pyrazolo [3,4-d] pyrimidines from Pyrimidine Derivatives
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Reactions of 1,3-disubstituted 6-chloro-5-formyluracils (1) with phenylhydrazine or methylhydrazine giving 1,5,7- and 2,5,7-trisubstituted 4,6-dioxo-4,5,6,7-tetrahydropyrazolo [3,4-d] pyrimidines (3,7 and 4) were investigated in detail. It was found out that 5-formyl group in 1 was more reactive than that 6-chloro group. Thus, under cold condition, the reaction of 1 with phenylhydrazine yielded Schiff's bases (2). Upon heating, 1 with equimolar or two equivalent moles of phenylhydrazine gave isomeric compounds, 3 and 4,which were also prepared by other routes. Reactions of methylhydrazine with 1 were also investigated. Furthermore, the Schiff's bases were made to react with other kinds of hydrazines. The reaction products showed that substituent at 1- or 2-position of the products (4,7) depended on the kind of hydrazine used later.
- 公益社団法人日本薬学会の論文
- 1972-02-25
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