Water → HCID 68015333, compound

HRID 570738Notes

Reaction equation

HRID 570738 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][OH:5].[H-].[Na+].Cl[C:9]1[C:14]2[N:15]=[C:16]([O:32][CH2:33][CH3:34])[N:17]([C:20]3[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]([F:31])([F:30])[F:29])=[CH:22][CH:21]=3)[C:18](=[O:19])[C:13]=2[CH:12]=[CH:11][N:10]=1.O>CN(C)C=O>[CH2:33]([O:32][C:16]1[N:17]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH2:27][C:28]([F:31])([F:30])[F:29])=[CH:22][CH:21]=2)[C:18](=[O:19])[C:13]2[CH:12]=[CH:11][N:10]=[C:9]([O:5][CH2:4][CH2:3][O:2][CH3:1])[C:14]=2[N:15]=1)[CH3:34]

Participants

6

Reactant 4

HCID 962WaterHCID 80192-MethoxyethanolHCID 24758Sodium hydrideHCID 86685395HCID 86685395, compound

Product 1

HCID 68015333HCID 68015333, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-methoxyethanol (0.019 ml) in N,N-dimethylformamide (3 ml) was added sodium hydride (60% in oil, 9 mg) at room temperature, and the mixture was stirred for 30 min. 8-Chloro-2-ethoxy-3-[4-(2,2,2-trifluoroethoxy)phenyl]pyrido[3,4-d]pyrimidin-4(3H)-one (80 mg) was added to reaction mixture, and the mixture was stirred at 60° C., for 5 hr, and allowed to be cooled to room temperature. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane). The obtained residue was suspended in a mixed solvent of ethyl acetate/hexane, and the resulting solid was collected by filtration to give the title compound (21 mg).

Workup

  1. stirringthe mixture was stirred at 60° C., for 5 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
  7. filtrationthe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-072f25e5d2444299919617b240d29dd3
Source dataset
uspto-grants-2015_05
Patent number
US09023858B2

Reaction notes

Loading…