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