Syntheses of antibacterial 2, 4-diamino-5-benzylpyrimidines. Ormetoprim and trimethoprim

PS Manchand, P Rosen, PS Belica…

Index: Manchand, Percy S.; Rosen, Perry; Belica, Peter S.; Oliva, Gloria V.; Perrotta, Agostino V.; Wong, Harry S. Journal of Organic Chemistry, 1992 , vol. 57, # 13 p. 3531 - 3535

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Citation Number: 23

Abstract

A general and mild method for the synthesis of 2, 4-diamino-5-benzylpyrimidines was achieved by the Friedel-Crafta reaction between 2-(methoxymethylene)-3- methoxypropanenitrile (10) and an activated aromatic substrate followed by treatment with guanidine. The method is illustrated by a synthesis of ormetoprim (2) in 75% overall yield from 3, 4-dimethoxytoluene (12). Efficient syntheses of trimethoprim (1) and 2 were also ...