4-Hydroxymethylpyridine → HCID 20491775, compound

Participants

Reaction Conditions

Reaction Steps

N,N-Dimethylformamide dineopentyl acetal (1.8 ml) was added to a stirred suspension of 5-chloropyrimidin-2-one (522 mg) and 4-pyridylcarbinol (611 mg) in dry N,N-dimethylformamide (10 ml) under nitrogen and the the mixture was then heated at 90° C. After 41/2 h the reaction mixture was evaporated to a brown solid which was subjected to column chromatography on silica developing and eluting with chloroform-ethanol, 14:1. This gave a yellow crystalline solid which was subjected to p.l.c. on silica developing with chloroform-ethanol, 9:1 (three runs). The major band was eluted with chloroform-ethanol, 1:1, to give a pale yellow foam which was crystallised from acetone to give off white crystals of the title pyrimidinone (210 mg), m.p. 205°-206° C., λmax (EtOH) 246 nm (ε 7.050), 332.5 nm (ε 950).

Provenance & Evidence