Pyrazolo[3,4-d]pyrimidine誘導体に関する研究(第9報)4-(p-Tolylsulfonyl)-1-phenyl-1H-pyrazolo[3,4-d]pyrimidineについて

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4-(p-Tolylsulfonyl)-1-phenyl-1H-pyrazolo [3,4-d] pyrimidine (I) is hydrolyzed by dil. hydrochloric acid into 1,5-dihydro-1-phenyl-4H-pyrazolo [3,4-d] pyrimidin-4-one (III), and the p-tolylsulfonyl group undergoes nucleophilic substitution with hydroxide, methoxide, hydrazine, butylamine, aniline, and cyanide. Application of active methylene compound, nitrile, or ketone in the presence of sodium amide results in substitution with a carbanion. When ketone is used as the carbanion source, reaction product differs with reaction conditions. For example, the use of acetone results in the formation of 1-(P-4-yl)-2-propanone (X_7) or 1,1-bis (P-4-yl)-2-pronone (X_7), where P-4-yl denotes 1-phenyl-1H-pyrazolo [3,4-d] pyrimidin-4-yl group. When 2-butanone (X_8) is used, the product is either 3-(P-4-yl)-2-butanone (X_<8-2>) or 1,1-bis (P-4-yl)-2-butanone (X_<8'-1>). In these cases, III is formed at the same time and its process of formation was discussed. In some cases, 5-(P-4-yl)-1,5-dihydro-1-phenyl-4H-pyrazolo [3,4-d] pyrimidin-4-one (XI) is formed as a by-product.
公益社団法人日本薬学会の論文
1978-01-25