Pyrimidine Derivatives and Related Compounds. XIII. The Synthesis of N-Substituted Pyrazolo [3. 4-d] pyrimidines from Pyrazole Derivatives
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An alkylation of 3-amino-4-ethoxycarbonylpyrazole (1) under various conditions was investigated. Alkylated pyrazoles (2,3a, b) were condensed with isocyanates or isothiocyanate to yield pyrazolylurea derivatives (4a-f, 10). Ring closure of these intermediates was carried out in a solution of sodium ethoxide and the resulting 2,5 (or 1,5)-disubstituted pyrazolo [3,4-d] pyrimidines (5a-f, 11a, b) were alkylated to give 2,5,7 (or 1,5,7)-trisubstituted pyrazolo [3,4-d] pyrimidines (6a-e, 12a, b) or 2,5-disubstituted 6-methylmercaptopyrazolo [3,4-d] pyrimidines (7a, b). Instead of the use of isocyanates, another methods by fusing ureas with methylpyrazole were also investigated. Furthermore, debenzylation of 2-benzylpyrazolo [3,4-d] pyrimidines (6c, d) was carried out with 35 atm of hydrogen in an autoclave at 220°over palladium on carbon to give debenzylated compounds (13a, b).
- 公益社団法人日本薬学会の論文
- 1972-02-25
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