Synthesis of 2,4-diaminothieno- and pyrrolo[2,3-d]pyrimidine-6-carboxylic acid derivatives

✍ Scribed by S. Tumkevicius; M. Dailide; A. Kaminskas

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2006
• Tongue: English
• Weight: 268 KB
• Volume: 43
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570430630

✦ Synopsis

Abstract

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A series of new 2,4‐diaminothieno[2,3‐d]‐ and 2,4‐diaminopyrrolo[2,3‐d]pyrimidine derivatives were synthesised. Reaction of 2‐amino‐4,6‐dichloropyrimidine‐5‐carbaldehyde (1) with ethyl mercaptoacetate, methyl N‐methylglycinate or ethyl glycinate afforded ethyl (2‐amino‐4‐chloro‐5‐formylpyrimidin‐6‐yl)thioacetate (2a), methyl N‐(2‐amino‐4‐chloro‐5‐formylpyrimidin‐6‐yl)‐N‐methylglycinate (2b) and ethyl N‐(2‐amino‐4‐chloro‐5‐formylpyrimidin‐6‐yl)glycinate (2c), respectively. Compounds 2a,b by treatment with bases cyclised to the corresponding 2‐amino‐4‐chlorothieno‐ and pyrrolo[2,3‐d]pyrimidine‐6‐carboxylates (3a,b). Heating 2,4‐diamino‐6‐chloropyrimidine‐5‐carbaldehyde (5) with ethyl mercaptoacetate or methyl N‐methylglycinate gave 2,4‐diaminothieno[2,3‐d]‐ and 2,4‐diaminopyrrolo[2,3‐d]‐pyrimidine‐6‐carboxylates (6a,b), whereas compound 5 with ethyl glycinate under the same reaction conditions afforded ethyl N‐(2,4‐diamino‐5‐formylpyrimidin‐6‐yl)glycinate (7). Treatment of 2,4‐diaminothieno[2,3‐d]pyrimidine‐6‐carboxylic acid (8a) with 4‐methoxy‐, 3,4,5‐trimethoxyanilines or ethyl N‐(4‐aminobenzoyl)‐L‐glutamate in the presence of dicyclohexylcarbodiimide and 1‐hydroxybenzotriazole furnished the corresponding N‐arylamides 9‐11.