Benzyl Alcohol → 7-(Benzyloxy)-3,4-dihydroquinazolin-4-one

Participants

Reaction Conditions

Reaction Steps

Benzyl alcohol (12.6 ml, 122 mmol) was added dropwise over 15 minutes to a slurry of sodium hydride (60% dispersion in mineral oil, 7.6 g, 190 mmol) in dimethylacetamide (100 ml) cooled in an ice-bath. The mixture was stirred at 0° C. for 15 minutes and then 7-fluoroquinazolin-4(3H)-one (prepared as described in WO03/055491) (10.0 g, 61 mmol) was added portionwise over 15 minutes. The mixture was warmed to room temperature and then heated at 60° C. for 15 hours and then at 80° C. for 3 hours. The mixture was poured into water (600 ml) and made acidic (pH˜6) by the addition of concentrated hydrochloric acid. The resultant precipitate was filtered and washed with water to yield 7-(benzyloxy)quinazolin-4(3H)-one as a colourless solid (11.5 g, 75% yield):

Provenance & Evidence