Acetone → racemic 3-[4-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1H-pyrazol-1-yl]cyclohexane-1,2-diol

HRID 595286Notes

Reaction equation

HRID 595286 reaction equation
C[N+]1([O-])CC[O:5]CC1.[CH:9]1([N:15]2[CH:19]=[C:18]([C:20]3[CH:21]=[C:22]([NH:27][C:28]4[N:33]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:31]=[CH:30][N:29]=4)[CH:23]=[C:24]([CH3:26])[CH:25]=3)[CH:17]=[N:16]2)CCC[CH:11]=[CH:10]1.[CH3:38][C:39]([CH3:41])=[O:40]>O.S([O-])([O-])(=O)=S.[Na+].[Na+].[Os](=O)(=O)(=O)=O>[CH3:26][C:24]1[CH:25]=[C:20]([C:18]2[CH:17]=[N:16][N:15]([CH:9]3[CH2:10][CH2:11][CH2:41][CH:39]([OH:40])[CH:38]3[OH:5])[CH:19]=2)[CH:21]=[C:22]([NH:27][C:28]2[N:33]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:31]=[CH:30][N:29]=2)[CH:23]=1

Participants

7

Reactant 3

HCID 180AcetoneHCID 82029Methyl morpholine oxideHCID 118208579racemic N-{3-[1-(cyclohex-2-en-1-yl)-1H-pyrazol-4-yl]-5-methylphenyl}-4-(trifluoromethyl)pyrimidin-2-amine

Product 1

HCID 118208695racemic 3-[4-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1H-pyrazol-1-yl]cyclohexane-1,2-diol

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 24477Sodium ThiosulfateSolvent

Procedure

Osmium tetroxide (2.08 mL, 0.34 mmol) and 4-methylmorpholine N-oxide (398 mg, 3.4 mmol) were added to a flask containing racemic N-{3-[1-(cyclohex-2-en-1-yl)-1H-pyrazol-4-yl]-5-methylphenyl}-4-(trifluoromethyl)pyrimidin-2-amine (339 mg, 0.85 mmol) dissolved in acetone (7.5 mL) and water (0.94 mL). The suspension was stirred for 2.5 hours at room temperature. The mixture was diluted with saturated aqueous sodium thiosulfate and stirred for 15 minutes at room temperature. The mixture was extracted with EtOAc (3×). The combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford racemic 3-[4-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1H-pyrazol-1-yl]cyclohexane-1,2-diol. MS ESI calcd. for C21H23F3N5O2 [M+H]+ 434. found 434.

Workup

  1. stirringstirred for 15 minutes at room temperature
  2. extractionThe mixture was extracted with EtOAc (3×)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7d2e8e5f5f424dd29a13ec4692a87725
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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