57506-37-3

Basic information

• Product Name: 4-(2,4-Diamino-pyrimidin-5-ylmethyl)-2,6-diethyl-phenol; hydrochloride
• CAS NO: 57506-37-3
• Molecular Weight: 308.811
• Mol File: 57506-37-3.mol

Chemical Properties

• CAS DataBase Reference: 4-(2,4-Diamino-pyrimidin-5-ylmethyl)-2,6-diethyl-phenol; hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(2,4-Diamino-pyrimidin-5-ylmethyl)-2,6-diethyl-phenol; hydrochloride(57506-37-3)
• EPA Substance Registry System: 4-(2,4-Diamino-pyrimidin-5-ylmethyl)-2,6-diethyl-phenol; hydrochloride(57506-37-3)

Safety Data

• Hazardous Substances Data: 57506-37-3(Hazardous Substances Data)

Upstream product

• 42310-45-2 2,4-diamino-5-hydroxymethyl-pyrimidine 
• 1006-59-3 2,6-diethylphenol 

Relevant articles and documents

2,4-Diamino-5-benzylpyrimidines and analogues as antibacterial agents. 6. A one-step synthesis of new trimethoprim derivatives and activity analysis by molecular modeling

A new route to 2,4-diamino-5-(4-hydroxybenzyl)pyrimidines has been developed that involves the condensation of 2,4-diamino-5-(hydroxymethyl)pyrimidine with phenols in acidic medium. The use of phenol and its 2,6-dialkyl derivatives produces 5-(4-hydroxybenzyl)pyrimidines exclusively. However, 2,6-dimethoxyphenol produces a mixture of 5-(3-hydroxy-2,4-dimethoxybenzyl)- and 5-(4-hydroxy-3,5-dimethoxybenzyl)pyrimidines. The phenolic condensation has been used to prepare a series of alkyl-substituted 5-(4-hydroxybenzyl)- and 5-(4-alkoxybenzyl)pyrimidines. The use of 1,2,3-trimethoxybenzene in place of a phenol produces 2,4-diamino-5-(2,3,4-trimethoxybenzyl)pyrimidine, a trimethoprim isomer with low antibacterial activity. The use of molecular models of several of the new orthosubstituted derivatives in the active site of dihydrofolate reductase has provided a rational explanation for their activities relative to trimethoprim.