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.

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Roth B, Strelitz JZ, Rauckman BS

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.

J Med Chem. 1980 Apr;23(4):379-84.

PubMed ID

6991692 [ View in PubMed

]

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.

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Binding Properties

Drug	Target	Property	Measurement	pH	Temperature (°C)
Trimethoprim	Dihydrofolate reductase	IC 50 (nM)	5	N/A	N/A	Details