SYNTHESIS OF METHYL ESTERS OF 5-AMINO-4-(SUBSTITUTED AMINO)-2-METHYLTHIO-7H-PYRROLO[2,3-<i>d</i>]PYRIMIDINE-6-CARBOXYLIC ACIDS

Abstract

The optimum route for the synthesis of methyl esters of N-[(4-substituted amino)-5-cyano-2-methylthiopyrimidin-6-yl]amino acids (which are starting materials for preparing the methyl esters of the corresponding 5-amino-4-(substituted amino)pyrrolo[2,3-d]pyrimidine-6-carboxylic acids) is via subsequent reactions of 4,6-dichloro-2-methylthiopyrimidine-5-carbonitrile with amines and methyl glycinate. In some examples, the reaction of methyl N-(4-chloro-2-methylthio-6-pyrimidinyl)aminoacetate with amines occurs to give the corresponding acid amides. The previously unknown synthesized derivatives of pyrimidin-6-yl amino acids and 4,5-diaminopyrrolo[2,3-d]pyrimidine-6-carboxylic acids possess fungicidal properties.

Authors: S. Tumkevicius, A. Urbonas, and P. Vainilavicius.

English Translation in Chemistry of Heterocyclic Compounds, 2000, 36 (7), pp 841-846

http://link.springer.com/article/10.1007/BF02256920