2,2,2-Trifluoroethanol → HCID 86685392, compound

HRID 570733Notes

Reaction equation

HRID 570733 reaction equation
[F:1][C:2]([F:6])([F:5])[CH2:3][OH:4].[H-].[Na+].C(S[C:13]1[N:14]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH2:32][C:33]([F:36])([F:35])[F:34])=[CH:27][CH:26]=2)[C:15](=[O:24])[C:16]2[CH:22]=[CH:21][NH:20][C:19](=[O:23])[C:17]=2[N:18]=1)CC>CN(C)C=O.[Cl-].[Na+].O>[F:1][C:2]([F:6])([F:5])[CH2:3][O:4][C:13]1[N:14]([C:25]2[CH:26]=[CH:27][C:28]([O:31][CH2:32][C:33]([F:36])([F:35])[F:34])=[CH:29][CH:30]=2)[C:15](=[O:24])[C:16]2[CH:22]=[CH:21][NH:20][C:19](=[O:23])[C:17]=2[N:18]=1

Participants

6

Reactant 3

HCID 64092,2,2-TrifluoroethanolHCID 24758Sodium hydrideHCID 68015323HCID 68015323, compound

Product 1

HCID 86685392HCID 86685392, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 2,2,2-trifluoroethanol (0.052 ml) in N,N-dimethylformamide (3 ml) was added sodium hydride (60% in oil, 24 mg) at room temperature, and the mixture was stirred for 5 min. A solution of 2-(propylsulfanyl)-3-[4-(2,2,2-trifluoroethoxy)phenyl]-3,7-dihydropyrido[3,4-d]pyrimidine-4,8-dione (535 mg) in N,N-dimethylformamide (3 ml) was added to the reaction mixture, and the mixture was stirred at 60° C. for 4 hr. The reaction mixture was allowed to be cooled to room temperature, saturated brine was added thereto, 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 (NH, methanol/ethyl acetate), and recrystallized from a mixed solvent of ethyl acetate/hexane to give the title compound (8 mg).

Workup

  1. stirringthe mixture was stirred at 60° C. for 4 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 (NH, methanol/ethyl acetate)
  7. customrecrystallized from a mixed solvent of ethyl acetate/hexane

Sources & evidence

ORD record
ord-01b228a7dd5a42c8a854929f6e2f4178
Source dataset
uspto-grants-2015_05
Patent number
US09023858B2

Reaction notes

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