Sodium borohydride → HCID 178428335, compound

HRID 2093812Notes

Reaction equation

HRID 2093812 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[N:14]=[C:13]([NH:15][C:16]3[CH:20]=[C:19]([CH3:21])[NH:18][N:17]=3)[C:12]([C:22]([F:25])([F:24])[F:23])=[CH:11][N:10]=2)[C:5]([CH3:26])=[CH:4][C:3]=1[CH:27]1[CH2:32][CH2:31][C:30](=[O:33])[CH2:29][CH2:28]1.[BH4-].[Na+]>CO>[CH3:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[N:14]=[C:13]([NH:15][C:16]3[CH:20]=[C:19]([CH3:21])[NH:18][N:17]=3)[C:12]([C:22]([F:24])([F:25])[F:23])=[CH:11][N:10]=2)[C:5]([CH3:26])=[CH:4][C:3]=1[C@H:27]1[CH2:28][CH2:29][C@H:30]([OH:33])[CH2:31][CH2:32]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 446211234-(2,5-dimethyl-4-(4-(5-methyl-1H-pyrazol-3-ylamino)-5-(trifluoromethyl)pyrimidin-2-ylamino)phenyl)cyclohexanone

Product 1

HCID 178428335HCID 178428335, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-(2,5-dimethyl-4-(4-(5-methyl-1H-pyrazol-3-ylamino)-5-(trifluoromethyl)pyrimidin-2-ylamino)phenyl)cyclohexanone (100 mg, 0.22 mmol) in MeOH (15 mL) was added NaBH4 (33.2 mg, 0.87 mmol). The reaction was stirred 30 for min., concentrated and purified by silica chromatography (MeOH/DCM: 8:92) to afford trans-4-(2,5-dimethyl-4-(4-(5-methyl-1H-pyrazol-3-ylamino)-5-(trifluoromethyl)pyrimidin-2-ylamino)phenyl)cyclohexanol; Rf: 0.35 (silica; MeOH/DCM 8:92); ESMS m/z 461.2 (M+H+).

Workup

  1. concentration, concentrated
  2. custompurified by silica chromatography (MeOH/DCM: 8:92)

Sources & evidence

ORD record
ord-33d39619d7a340ae903a93f1a1f94302
Source dataset
uspto-grants-2013_05
Patent number
US08445505B2

Reaction notes

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