Ammonium formate → 7-hydroxy-5-isopropoxyquinazolin-4(3H)-one

HRID 639981Notes

Reaction equation

HRID 639981 reaction equation
C([O-])=O.[NH4+].C([O:12][C:13]1[CH:22]=[C:21]2[C:16]([C:17](=[O:23])[NH:18][CH:19]=[N:20]2)=[C:15]([O:24][CH:25]([CH3:27])[CH3:26])[CH:14]=1)C1C=CC=CC=1>[Pd].CN(C)C=O>[OH:12][C:13]1[CH:22]=[C:21]2[C:16]([C:17](=[O:23])[NH:18][CH:19]=[N:20]2)=[C:15]([O:24][CH:25]([CH3:27])[CH3:26])[CH:14]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 1355106847-(benzyloxy)-5-isopropoxyquinazolin-4(3H)-one

Product 1

HCID 1363551707-hydroxy-5-isopropoxyquinazolin-4(3H)-oneYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

Ammonium formate (9.5 g, 150 mmol) and 10% palladium on carbon (500 mg) were added to a solution of 7-(benzyloxy)-5-isopropoxyquinazolin-4(3H)-one (4.6 g, 15.0 mmol) in dimethylformamide (40 ml) and the mixture stirred at ambient temperature for 4 hours. The mixture was filtered through Celite and then evaporated under reduced pressure. The residue was stirred in water (100 ml) for 30 minutes and then filtered and washed with water (25 ml) and then dried to leave 7-hydroxy-5-isopropoxyquinazolin-4(3H)-one (3.3 g, 100% yield) as a white solid:

Workup

  1. filtrationThe mixture was filtered through Celite
  2. customevaporated under reduced pressure
  3. stirringThe residue was stirred in water (100 ml) for 30 minutes
  4. filtrationfiltered
  5. washwashed with water (25 ml)
  6. customdried

Sources & evidence

ORD record
ord-a45ee6397e5249c299aca46e86a42b36
Source dataset
uspto-grants-2010_04
Patent number
US07691867B2

Reaction notes

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