Acetone → 1-(2-(3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-6-(1-(2,2,2-trifluoroethoxy)-ethyl)pyrimidin-4-yl)ethanol

HRID 59137Notes

Reaction equation

HRID 59137 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:15][C:16]2[N:21]=[C:20]([C:22](=[O:24])[CH3:23])[CH:19]=[C:18]([CH:25]([O:27][CH2:28][C:29]([F:32])([F:31])[F:30])[CH3:26])[N:17]=2)[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1.[BH4-].[Na+].CC(C)=O>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:15][C:16]2[N:21]=[C:20]([CH:22]([OH:24])[CH3:23])[CH:19]=[C:18]([CH:25]([O:27][CH2:28][C:29]([F:30])([F:31])[F:32])[CH3:26])[N:17]=2)[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1

Participants

5

Reactant 3

HCID 180AcetoneHCID 4311764Sodium borohydrideHCID 117824086HCID 117824086, compound

Product 1

HCID 863442481-(2-(3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-6-(1-(2,2,2-trifluoroethoxy)-ethyl)pyrimidin-4-yl)ethanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(2-(3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-6-(1-(2,2,2-trifluoroethoxy)-ethyl)pyrimidin-4-yl)ethanone (90 mg, 0.20 mmol) was dissolved in ethanol (5 mL). Sodium borohydride (30.3 mg, 0.80 mmol) was added in portions. The mixture was stirred at rt for 10 min. Acetone (2 mL) was added and the mixture was stirred for 20 min. The mixture was filtered, the volatiles were removed in vacuum, and the residue was purified by preparative HPLC to yield the title compound consisting of four stereoisomers, 64 mg (71%).

Workup

  1. stirringthe mixture was stirred for 20 min
  2. filtrationThe mixture was filtered
  3. customthe volatiles were removed in vacuum
  4. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-f765abbd2d6e41399e5c3df401d1f5e4
Source dataset
uspto-grants-2016_09
Patent number
US09439904B2

Reaction notes

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