PMID: 6991692Apr 1, 1980Paper

2,4-Diamino-5-benzylpyrimidines and analogues as antibacterial agents. 2. C-Alkylation of pyrimidines with Mannich bases and application to the synthesis of trimethoprim and analogues

Journal of Medicinal Chemistry
B RothB S Rauckman

Abstract

A new route to 5-(p-hydroxybenzyl)pyrimidines has been developed which utilizes phenolic Mannich bases plus pyrimidines containing at least two activating groups. The products can be alkylated on the phenolic oxygen or on the pyrimidine N-1 atom, depending on conditions. This method has been used to prepare trimethoprim, a broad-spectrum antibacterial agent, starting from 2,4-diaminopyrimidine and 2,6-dimethoxyphenol.

Citations

Apr 6, 1981·FEBS Letters·D J BakerD K Stammers
Sep 1, 1981·Biomedical Mass Spectrometry·D A BrentT R Brunner
Sep 5, 2012·Pathogens and Global Health·P R C CorrêaS F Yamada-Ogatta
Apr 17, 2018·Bioconjugate Chemistry·Xiaojian WangNiren Murthy

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