1,1-Bis(2,2-dimethylpropoxy)-N,N-dimethylmethanamine → 5-Chloro-1-(1-methylpyrrol-2-ylmethyl)pyrimidin-2-one

Participants

Reaction Conditions

Reaction Steps

N,N-Dimethylformamide dineopentyl acetal (3.04 ml) was added to a stirred suspension of 5-chloropyrimidin-2-one (881 mg) and N-methyl-2-hydroxymethylpyrrole (1.050 g) in dry N,N-dimethylformamide (17 ml) under nitrogen. The resulting pale yellow solution was then stirred and heated at 90° C. under nitrogen. After 1 h the reaction mixture was evaporated to a brown crystalline solid (1.891 g). The solid was subjected to column chromatography on silica (70-230 mesh) (200 g) developing with chloroform-ethanol, 29:1. The resulting pale brown crystalline solid (1.479 g) was crystallised twice from acetone to give off white needles of the title pyrrole (559 mg), m.p. 137°-141° C., λmax 226.5 nm (ε 15,920), 334 nm (ε 2,680).

Provenance & Evidence