Methanol → 2-(2,6-dimethyl-pyridin-4-yl)-7-fluoro-5-methoxy-3H-quinazolin-4-one

HRID 591808Notes

Reaction equation

HRID 591808 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[NH:17][C:16](=[O:18])[C:15]3[C:10](=[CH:11][C:12]([F:20])=[CH:13][C:14]=3F)[N:9]=2)[CH:5]=[C:4]([CH3:21])[N:3]=1.[CH3:22][O-:23].[Na+].CO.O>CN(C=O)C.C(O)(=O)C>[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[NH:17][C:16](=[O:18])[C:15]3[C:10](=[CH:11][C:12]([F:20])=[CH:13][C:14]=3[O:23][CH3:22])[N:9]=2)[CH:5]=[C:4]([CH3:21])[N:3]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 962WaterHCID 10942334Sodium MethoxideHCID 1363480062-(2,6-dimethylpyridin-4-yl)-5,7-difluoro-3H-quinazolin-4-one

Product 1

HCID 1363480402-(2,6-dimethyl-pyridin-4-yl)-7-fluoro-5-methoxy-3H-quinazolin-4-one

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of 2-(2,6-dimethyl-pyridin-4-yl)-5,7-difluoro-3H-quinazolin-4-one (0.72 g, 2.51 mmol) in DMF (10 mL), a solution of sodium methoxide in methanol (25 wt %, 1.36 g, 25.1 mmol) was added and the reaction mixture was stirred at room temperature for 16 hours. Water was added, the mixture was acidified to pH approximately 4-5 with acetic acid, and the precipitated solid was filtered and dried under vacuum, to give 2-(2,6-dimethyl-pyridin-4-yl)-7-fluoro-5-methoxy-3H-quinazolin-4-one as a light yellow solid. Yield: 0.28 g (37%).

Workup

  1. filtrationthe precipitated solid was filtered
  2. customdried under vacuum

Sources & evidence

ORD record
ord-ef52fd7235e84734865151039e228f9a
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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