(7-(Benzyloxy)-6-methoxy-4-oxoquinazolin-3(4H)-yl)methyl pivalate → (7-Hydroxy-6-methoxy-4-oxoquinazolin-3(4H)-yl)methyl pivalate

Participants

Reaction Steps

10% palladium on carbon (420 mg) was added to a solution of 7-benzyloxy-6-methoxy-3-pivaloyloxymethyl-3,4-dihydroquinazolin-4-one (4.17 g) in dimethylformamide (30 ml), methanol (30 ml), ethyl acetate (150 ml) and acetic acid (0.42 ml). Hydrogen gas was bubbled into the reaction and it was then stirred at ambient temperature for 18 hours. Reaction was poured through diatomaceous earth (Celite®) and the filtrate was evaporated to dryness and then triturated with diethyl ether and dried to yield 7-hydroxy-6-methoxy-3-pivaloyloxymethyl-3,4-dihydroquinazolin-4-one as a solid, (2.51 g, 78%). NMR: 1.10 (s, 9H), 3.88 (s, 3H), 5.86 (s, 2H), 6.96 (s, 1H), 7.46 (s, 1H), 8.29 (s, 1H); m/s: M+H+ 307.

Provenance & Evidence