Potassium Carbonate → racemic 5-{[4-(3-{[4-(difluoromethyl)pyrimidin-2-yl]amino}-5-methylphenyl)-1H-pyrazol-1-yl]methyl}-4-(hydroxymethyl)-1,3-oxazolidin-2-one

HRID 595333Notes

Reaction equation

HRID 595333 reaction equation
FC(F)(F)C([O:5][CH2:6][CH:7]1[CH:11]([CH2:12][N:13]2[CH:17]=[C:16]([C:18]3[CH:23]=[C:22]([CH3:24])[CH:21]=[C:20]([NH:25][C:26]4[N:31]=[C:30]([CH:32]([F:34])[F:33])[CH:29]=[CH:28][N:27]=4)[CH:19]=3)[CH:15]=[N:14]2)[O:10][C:9](=[O:35])[NH:8]1)=O.C(=O)([O-])[O-].[K+].[K+]>CO.O>[F:34][CH:32]([F:33])[C:30]1[CH:29]=[CH:28][N:27]=[C:26]([NH:25][C:20]2[CH:19]=[C:18]([C:16]3[CH:15]=[N:14][N:13]([CH2:12][CH:11]4[O:10][C:9](=[O:35])[NH:8][CH:7]4[CH2:6][OH:5])[CH:17]=3)[CH:23]=[C:22]([CH3:24])[CH:21]=2)[N:31]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 118208619(5-{[4-(3-{[4-(difluoromethyl)pyrimidin-2-yl]amino}-5-methylphenyl)-1H-pyrazol-1-yl]methyl}-2-oxo-1,3-oxazolidin-4-yl)methyl trifluoroacetate

Product 1

HCID 118208809racemic 5-{[4-(3-{[4-(difluoromethyl)pyrimidin-2-yl]amino}-5-methylphenyl)-1H-pyrazol-1-yl]methyl}-4-(hydroxymethyl)-1,3-oxazolidin-2-one

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of (5-{[4-(3-{[4-(difluoromethyl)pyrimidin-2-yl]amino}-5-methylphenyl)-1H-pyrazol-1-yl]methyl}-2-oxo-1,3-oxazolidin-4-yl)methyl trifluoroacetate (80 mg, 0.15 mmol) and potassium carbonate (80 mg, 0.58 mmol) in methanol (3 mL) was stirred at 25° C. for 30 minutes. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford the crude product residue. The crude product residue was purified by prep-TLC (ethyl acetate) to give racemic 5-{[4-(3-{[4-(difluoromethyl)pyrimidin-2-yl]amino}-5-methylphenyl)-1H-pyrazol-1-yl]methyl}-4-(hydroxymethyl)-1,3-oxazolidin-2-one. MS ESI calc'd. for C20H21F2N6O3 [M+H]+ 431. found 431.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto afford the crude product residue
  6. customThe crude product residue was purified by prep-TLC (ethyl acetate)

Sources & evidence

ORD record
ord-d6559652d59d427d866bc0c3650a9b6d
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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