Water → HCID 86685360, compound

HRID 570697Notes

Reaction equation

HRID 570697 reaction equation
[H-].[Na+].[F:3][C:4]([F:10])([CH2:7][O:8][CH3:9])[CH2:5][OH:6].C(S[C:15]1[N:16]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH2:34][C:35]([F:38])([F:37])[F:36])=[CH:29][CH:28]=2)[C:17](=[O:26])[C:18]2[CH:24]=[CH:23][C:22](=[O:25])[NH:21][C:19]=2[N:20]=1)CC.O>O1CCCC1>[F:3][C:4]([F:10])([CH2:7][O:8][CH3:9])[CH2:5][O:6][C:15]1[N:16]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH2:34][C:35]([F:36])([F:38])[F:37])=[CH:29][CH:28]=2)[C:17](=[O:26])[C:18]2[CH:24]=[CH:23][C:22](=[O:25])[NH:21][C:19]=2[N:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 866619421247089-57-1HCID 86685358HCID 86685358, compound

Product 1

HCID 86685360HCID 86685360, compoundYield 4.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of sodium hydride (60% in oil, 29 mg) in tetrahydrofuran (5 ml) was added 2,2-difluoro-3-methoxypropan-1-ol (151 mg) at room temperature, and the mixture was stirred at room temperature for 10 min. To the reaction mixture was added 2-(propylsulfanyl)-3-[4-(2,2,2-trifluoroethoxy)phenyl]pyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione (165 mg), and the mixture was stirred at room temperature for 5 hr. The reaction mixture was added to 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), and recrystallized from a mixed solvent of hexane/ethyl acetate to give the title compound (8 mg).

Workup

  1. stirringthe mixture was stirred at room temperature 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. customrecrystallized from a mixed solvent of hexane/ethyl acetate

Sources & evidence

ORD record
ord-559d34b6ea3a44a2a78a3ccf7e613ee5
Source dataset
uspto-grants-2015_05
Patent number
US09023858B2

Reaction notes

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