Water → HCID 136348017, compound

HRID 591823Notes

Reaction equation

HRID 591823 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][OH:5].[H-].[Na+].[CH3:8][C:9]1[CH:14]=[C:13]([C:15]2[NH:24][C:23](=[O:25])[C:22]3[C:17](=[CH:18][C:19]([F:27])=[CH:20][C:21]=3F)[N:16]=2)[CH:12]=[C:11]([CH3:28])[N:10]=1.O>CN(C=O)C.C(O)(=O)C>[CH3:8][C:9]1[CH:14]=[C:13]([C:15]2[NH:24][C:23](=[O:25])[C:22]3[C:17](=[CH:18][C:19]([F:27])=[CH:20][C:21]=3[O:5][CH2:4][CH2:3][O:2][CH3:1])[N:16]=2)[CH:12]=[C:11]([CH3:28])[N:10]=1

Participants

7

Reactant 4

HCID 962WaterHCID 80192-MethoxyethanolHCID 24758Sodium hydrideHCID 1363480062-(2,6-dimethylpyridin-4-yl)-5,7-difluoro-3H-quinazolin-4-one

Product 1

HCID 136348017HCID 136348017, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-methoxyethanol (2.65 g, 34.8 mmol) in DMF (38 mL) was added sodium hydride (60% suspension in mineral oil, 0.70 g, 17.4 mmol) in portions and the reaction mixture was stirred at room temperature for 0.5 hours. To this mixture was added 2-(2,6-dimethylpyridin-4-yl)-5,7-difluoro-3H-quinazolin-4-one (0.50 g, 1.74 mmol) and the reaction mixture was stirred at room temperature for 16 hours. Water (1.5 mL) was added, the mixture was neutralized to pH approximately 6-7 with acetic acid, concentrated, dissolved in ethyl acetate (200 mL), washed with water and brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was washed with hexanes to give 2-(2,6-dimethylpyridin-4-yl)-7-fluoro-5-(2-methoxyethoxy)-3H-quinazolin-4-one) as a pale solid. Yield: 0.52 g (87%).

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 16 hours
  2. concentrationconcentrated
  3. dissolutiondissolved in ethyl acetate (200 mL)
  4. washwashed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. washThe residue was washed with hexanes

Sources & evidence

ORD record
ord-fcbc2b868eac43c287569e6d971ebf54
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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