6981-04-0

Basic information

• Product Name: 5-(2,3,4-trimethoxy-benzyl)-pyrimidine-2,4-diamine
• Synonyms: 5-(2,3,4-trimethoxy-benzyl)-pyrimidine-2,4-diamine
• CAS NO: 6981-04-0
• Molecular Weight: 290.322
• Mol File: 6981-04-0.mol

Chemical Properties

• CAS DataBase Reference: 5-(2,3,4-trimethoxy-benzyl)-pyrimidine-2,4-diamine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(2,3,4-trimethoxy-benzyl)-pyrimidine-2,4-diamine(6981-04-0)
• EPA Substance Registry System: 5-(2,3,4-trimethoxy-benzyl)-pyrimidine-2,4-diamine(6981-04-0)

Safety Data

• Hazardous Substances Data: 6981-04-0(Hazardous Substances Data)

Upstream product

• 50-01-1 guanidine hydrochloride 
• 84876-26-6 3-morpholino-2-(2,3,4-trimethoxybenzyl)acrylonitrile 
• 110-67-8 3-Methoxypropionitrile 
• 113-00-8 guanidine nitrate 
• 2103-57-3 2,3,4-trimethoxybenzaldehyde 
• 42310-45-2 2,4-diamino-5-hydroxymethyl-pyrimidine 
• 634-36-6 1,2,3-trimethoxybenzene 

Downstream Products

• 84876-27-7 2,4-diamino-5-(3-hydroxy-2,4-dimethoxybenzyl)pyrimidine 
• 83322-41-2 2,4-diamino-5-(4-hydroxy-3,5-dimethoxybenzyl)pyrimidine 

Relevant articles and documents

Quantitative structure-activity relationships of 2,4-diamino-5-(2-X- benzyl)pyrimidines versus bacterial and avian dihydrofolate reductase

Quantitative structure-activity relationships (QSAR) have been formulated for a set of 15 2,4-diamino-5-(2-X-benzyl)pyrimidines versus dihydrofolate reductase from Lactobacillus casei and chicken liver. QSARs were also developed for comprehensive data sets containing mono-, di-, and trisubstituted benzyl derivatives. Particular emphasis was placed on the role played by ortho substituents in the overall binding process and subsequent inhibition of the catalytic process in both the prokaryotic and eucaryotic DHFRs. Comparisons between the two QSARs reveal subtle differences at specific positions which can be optimized to design more selective antibacterial agents.

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.