Acetic Acid → 7-Fluoro-5-isopropoxy-3,4-dihydroquinazolin-4-one

HRID 749193Notes

Reaction equation

HRID 749193 reaction equation
F[C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]2[C:3]=1[C:4](=[O:13])[NH:5][CH:6]=[N:7]2.[CH:14]([OH:17])([CH3:16])[CH3:15].[H-].[Na+].C(O)(=O)C>CN(C)C=O>[F:12][C:10]1[CH:9]=[C:8]2[C:3]([C:4](=[O:13])[NH:5][CH:6]=[N:7]2)=[C:2]([O:17][CH:14]([CH3:16])[CH3:15])[CH:11]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 3776IsopropanolHCID 24758Sodium hydrideHCID 1355106875,7-Difluoro-3,4-dihydroquinazolin-4-one

Product 1

HCID 1362314007-Fluoro-5-isopropoxy-3,4-dihydroquinazolin-4-oneYield 95.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5,7-Difluoroquinazolin-4(3H)one (2.73 g, 15 mmol) in dimethylformamide (20 ml) was reacted with isopropanol (1.26 ml, 16.4 mmol) and sodium hydride (1.8 g, 45 mmol) at 0° C. under argon. The mixture was stirred at ambient temperature for 14 hours, acidified with acetic acid and concentrated. The residue was washed with water and dried to yield 7-fluoro-5-isopropoxyquinazolin-4(3H)-one (3.17 g, 95% yield) as a beige solid:

Workup

  1. concentrationconcentrated
  2. washThe residue was washed with water
  3. customdried

Sources & evidence

ORD record
ord-ca079afa492d499684578f44d5299344
Source dataset
uspto-grants-2008_07
Patent number
US07402585B2

Reaction notes

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