Methanol → 7-fluoro-5-methoxy-2-pyridin-4-yl-3H-quinazolin-4-one

HRID 591799Notes

Reaction equation

HRID 591799 reaction equation
F[C:2]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]2[C:3]=1[C:4](=[O:19])[NH:5][C:6]([C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1)=[N:7]2.[CH3:20][O-:21].[Na+].CO.O>CN(C=O)C.C(O)(=O)C>[F:12][C:10]1[CH:9]=[C:8]2[C:3]([C:4](=[O:19])[NH:5][C:6]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)=[N:7]2)=[C:2]([O:21][CH3:20])[CH:11]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 962WaterHCID 10942334Sodium MethoxideHCID 1363794005,7-difluoro-2-pyridin-4-yl-3H-quinazolin-4-one

Product 1

HCID 1363480537-fluoro-5-methoxy-2-pyridin-4-yl-3H-quinazolin-4-one

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of 5,7-difluoro-2-pyridin-4-yl-3H-quinazolin-4-one (0.20 g, 0.80 mmol) in DMF (3 mL) was added sodium methoxide in methanol (0.43 g, 8.0 mmol) and the reaction mixture was stirred at room temperature for 16 hours. Water was added, the mixture was acidified with acetic acid to pH approximately 4-5, and the precipitated solid was filtered off to obtain 7-fluoro-5-methoxy-2-pyridin-4-yl-3H-quinazolin-4-one as a yellowish solid. Yield: 0.20 g (83%).

Workup

  1. filtrationthe precipitated solid was filtered off

Sources & evidence

ORD record
ord-69d7f965874e4b4c8ae05f4b31332b45
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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