53645-66-2

Basic information

• Product Name: 1H-Pyrazolo[3,4-d]pyrimidine, 1-methyl-4-(phenylmethyl)-
• CAS NO: 53645-66-2
• Molecular Formula: C13H12N4
• Molecular Weight: 224.265
• Mol File: 53645-66-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 1H-Pyrazolo[3,4-d]pyrimidine, 1-methyl-4-(phenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Pyrazolo[3,4-d]pyrimidine, 1-methyl-4-(phenylmethyl)-(53645-66-2)
• EPA Substance Registry System: 1H-Pyrazolo[3,4-d]pyrimidine, 1-methyl-4-(phenylmethyl)-(53645-66-2)

Safety Data

• Hazardous Substances Data: 53645-66-2(Hazardous Substances Data)

Upstream product

• 59564-09-9 (4-methoxy-phenyl)-(1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-yl)-methanone 

Relevant articles and documents

Carbon-carbon bond cleavage of α-hydroxybenzylheteroarenes catalyzed by cyanide ion: Retro-benzoin condensation affords ketones and heteroarenes and benzyl migration affords benzylheteroarenes and arenecarbaldehydes

4-(α-Benzylα-hydroxybenzyl)quinazoline (4a) underwent retro-benzoin condensation catalyzed by cyanide ion to give deoxybenzoin (2a) and quinazoline (5a). Similarly, several nitrogen-containing heteroarenes (4, 9, 12, 16-19) having an α-hydroxybenzyl group at the α-position of the nitrogen underwent retro-benzoin type condensation to afford kelones (2) and heteroarenes (5). However, similar reaction of pyrazolopyrimidines (13, 14, 15) having an α-benzyl-α-hydroxybelzyl group resulted in benzyl migration, giving benzylpyrazolopyrimidines (8) and arenecarbaldehydes (3). Tetrabutylammonium cyanide (11, Bu4NCN) was a more effective cyanide ion donor than KCN (10). The retro-benzoin condensation was applied to the synthesis of 2-substituted quinazolines (38) from 2-chloro-4- aroylquinazolines (34), using the aroyl group as a protecting and electron- withdrawing group.