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

HRID 1372983Notes

Reaction equation

HRID 1372983 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

HCID 10834555(7-(Benzyloxy)-6-methoxy-4-oxoquinazolin-3(4H)-yl)methyl pivalate

Product 1

HCID 10804576(7-Hydroxy-6-methoxy-4-oxoquinazolin-3(4H)-yl)methyl pivalateYield 80.4%

Reagents, catalysts & solvents 5

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 7-benzyloxy-6-methoxy-3-(pivaloyloxymethyl)-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-(pivaloyloxymethyl)-3,4-dihydroquinazolin-4-one (4.36 g, 80%).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent removed from the filtrate by evaporation
  3. customThe residue was triturated with ether
  4. filtrationcollected by filtration
  5. customdried under vacuum

Sources & evidence

ORD record
ord-0167c2990ca14bc6a3c697029ab614e0
Source dataset
uspto-grants-2007_01
Patent number
US07160889B2

Reaction notes

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