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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 37, 2007 - Issue 13
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Original Articles

General and Facial Synthesis of 2‐Amino‐5‐halogenpyrimidine‐4‐carboxylic Acids and Their Derivatives

, &
Pages 2231-2241 | Received 04 Nov 2006, Published online: 03 Jul 2007
 

Abstract

A facile synthetic approach to 2‐amino‐5‐halogen‐pyrimidine‐4‐carboxylic acids from 5‐halogen‐2‐methylsulfonylpyrimidine‐4‐carboxylic acid by nucleophilic displacement of the methylsulfonyl group with primary and secondary aliphatic amines has been developed. The titled amino acids underwent decarboxylation, yielding 2‐amino‐5‐halogenpyrimidines. Starting from 2‐amino‐5‐chloropyrimidine‐4‐carboxylic acid chlorides, 2‐[5‐chloro‐2‐(amino)‐4‐pyrimidinyl]‐2‐oxo‐1‐(2‐pyridyl)‐ethyl cyanides were obtained in excellent yields.

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