(7-(Benzyloxy)-6-methoxy-4-oxoquinazolin-3(4H)-yl)methyl pivalate → (7-Hydroxy-6-methoxy-4-oxoquinazolin-3(4H)-yl)methyl pivalate
Reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](=[O:27])[N:14]([CH2:19][O:20][C:21](=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23])[CH:15]=[N:16]2)=[CH:11][C:10]=1[O:28][CH3:29])C1C=CC=CC=1>[Pd].CN(C)C=O.CO.C(OCC)(=O)C.C(O)(=O)C>[OH:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](=[O:27])[N:14]([CH2:19][O:20][C:21](=[O:26])[C:22]([CH3:23])([CH3:24])[CH3:25])[CH:15]=[N:16]2)=[CH:11][C:10]=1[O:28][CH3:29]Participants
7
Reactant 1
Product 1
Reagents, catalysts & solvents 5
Procedure
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.
Workup
- customHydrogen gas was bubbled into the reaction and it
- customReaction
- additionwas poured through diatomaceous earth (Celite®)
- customthe filtrate was evaporated to dryness
- customtriturated with diethyl ether
- customdried
Sources & evidence
- ORD record
- ord-051858f41a8b420294c6dc3b69e1e00d
- Source dataset
- uspto-grants-2003_07
- Patent number
- US06593333B1
Reaction notes
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