(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].C(OCC)(=O)C.CN(C=O)C.CO.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
A mixture of 7-benzyloxy-6-methoxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (7 g, 17.7 mmol) and 10% palladium-on-charcoal catalyst (700 mg) in ethyl acetate (250 ml), DMF (50 ml), methanol (50 ml) and acetic acid (0.7 ml) was stirred under hydrogen at atmospheric pressure for 40 minutes. The catalyst was removed by filtration and the solvent removed from the filtrate by evaporation. The residue was triturated with ether, collected by filtration and dried under vacuum to give 7-hydroxy-6-methoxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (4.36 g, 80%). 1H NMR Spectrum: (DMSOd6) 1.1(s, 9H); 3.89(s, 3H); 5.89(s, 2H); 7.0(s, 1H); 7.48(s, 1H); 8.5(s, 1H)
Workup
- customThe catalyst was removed by filtration
- customthe solvent removed from the filtrate by evaporation
- customThe residue was triturated with ether
- filtrationcollected by filtration
- customdried under vacuum
Sources & evidence
- ORD record
- ord-66309759234044dbac4591ea45102dda
- Source dataset
- uspto-grants-2001_07
- Patent number
- US06258951B1
Reaction notes
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