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Synthesis of 7H-tetrazolo[1,5-c]pyrrolo[3,2-e]pyrimidines and their reductive ring cleavage to 4-aminopyrrolo[2,3-d]pyrimidines

✍ Scribed by Chaitanya G. Dave; Rina D. Shah

Publisher: Journal of Heterocyclic Chemistry
Year: 1998
Tongue: English
Weight: 336 KB
Volume: 35
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570350609

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✦ Synopsis

Abstract

Some new 7,9‐disubstituted 7__H__‐1,2,3,4‐tetrazolo[1,5‐c]pyrrolo[3,2‐e]pyrimidines 5 have been synthesized either by diazotization of 4‐hydrazino‐5,7‐disubstituted‐7__H__‐pyrrolo[2,3‐d]pyrimidines 4 obtained by hydrazinolysis of 4‐chloro‐5,7‐disubstituted‐7__H__‐pyrrolo[2,3‐d]pyrimidines 3 or via a substitution reaction between 3 and sodium azide. 5,7‐Disubstituted‐7__H__‐pyrrolo[2,3‐d]pyrimidin‐4(3__H__)‐ones 2 were obtained by cyclocondensation of 2‐amino‐3‐cyano‐1,4‐disubstituted pyrroles 1 with formic acid which on chlorination using phosphorus oxychloride afforded 3. A novel route for the synthesis of 4‐amino‐5,7‐disubstituted‐7__H__‐pyrrolo[2,3‐d]pyrimidines 6 by the reductive ring cleavage of 5 has been reported.

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