17326-35-1

Usage

Structure

Pyrimidine derivative with a bromomethyl group attached to the 5th carbon atom of the pyrimidine ring

Usage

Intermediate in the synthesis of pharmaceuticals and agrochemicals, production of dyes, pigments, and other industrial chemicals, and a building block for the preparation of various organic compounds with diverse applications

Bromomethyl group

Makes it a versatile building block for the preparation of various organic compounds

Research and development

Studied for its potential use in chemical research and development

Upstream product

• 42310-45-2 2,4-diamino-5-hydroxymethyl-pyrimidine 

Downstream Products

• 1006-59-3 2,6-diethylphenol 

Relevant academic research and scientific papers

Probing riboswitch-ligand interactions using thiamine pyrophosphate analogues

The Escherichia coli thiM riboswitch forms specific contacts with its natural ligand, thiamine pyrophosphate (TPP or thiamine diphosphate), allowing it to generate not only nanomolar binding affinity, but also a high degree of discrimination against similar small molecules. A range of synthetic TPP analogues have been used to probe each of the riboswitch-ligand interactions. The results show that the pyrimidine-sensing helix of thiM is exquisitely tuned to select for TPP by recognising the H-bonding donor and acceptors around its aminopyrimidine ring and also by forming π-stacking interactions that may be sensitive to the electronics of the ring. The central thiazolium ring of TPP appears to be more important for ligand recognition than previously thought. It may contribute to binding via long-range electrostatic interactions and/or by exerting an electron withdrawing effect on the pyrimidine ring, allowing its presence to be sensed indirectly and thereby allowing discrimination between thiamine (and its phosphate esters) and other aminopyrimidines found in vivo. The pyrophosphate moiety is essential for submicromolar binding affinity, but unexpectedly, it does not appear to be strictly necessary for modulation of gene expression.

Process for substituted 5-benzyl-2,4-diamino-pyrimidines

A process for preparing a compound of the formula STR1 wherein R1 and R2 are lower alkoxy or taken together are METHYLENEDIOXY; R3 is lower alkyl or hydrogen, which comprises the step of reacting an aromatic compound of the formula STR2 wherein R1, R2 and R3 are as previously described, with a diamino-pyrimidine of the formula STR3 wherein R4 is lower alkoxy, benzyloxy, hydroxy or halogen, in the presence of an inorganic or organic acid selected from the group consisting of ortho-phosphoric acid, poly-phosphoric acid, hydrohalic acids and tri-haloacetic acids, at a temperature in the range of from about 50° C. to about 110° C., is described.