Ammonium formate → 6-Methoxy-7-hydroxyquinazolin-4-one

HRID 639958Notes

Reaction equation

HRID 639958 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](=[O:19])[NH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:20][CH3:21])C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].CN(C)C=O>[OH:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](=[O:19])[NH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:20][CH3:21]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 1354047187-Benzyloxy-6-methoxy-3H-quinazolin-4-one

Product 1

HCID 1356099526-Methoxy-7-hydroxyquinazolin-4-oneYield 64%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

Palladium on carbon (3.3 g of a 10% mixture) was added to a solution of 7-(benzyloxy)-6-methoxyquinazolin-4-(3H)-one (20 g, 71 mmol) (prepared according to J. Med. Chem. 1999, 42, 5369-5389) was suspended in dimethylformamide (530 ml). Ammonium formate (45 g, 710 mmol) was then added portion wise over 1.25 hours. The reaction mixture was stirred for an additional 0.5 hours and the catalyst was removed by filtration. The solvent was removed in vacuo to yield 7-hydroxy-6-methoxyquinazolin-4-(3H)-one (8.65 g, 64% yield):

Workup

  1. customthe catalyst was removed by filtration
  2. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-674c0a70693640efb8563ec362cb9e0e
Source dataset
uspto-grants-2010_04
Patent number
US07691867B2

Reaction notes

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