Acetic Acid → 1-(2-(3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-5-methyl-6-((2,2,2-trifluoroethoxy)methyl)pyrimidin-4-yl)ethanol

HRID 59136Notes

Reaction equation

HRID 59136 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])[C:19]([CH3:25])=[C:18]([CH2:26][O:27][CH2:28][C:29]([F:32])([F:31])[F:30])[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+].C(O)(=O)C>O1CCOCC1.O>[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])[C:19]([CH3:25])=[C:18]([CH2:26][O:27][CH2:28][C:29]([F:30])([F:31])[F:32])[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

6

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 117823951HCID 117823951, compound

Product 1

HCID 863442491-(2-(3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-5-methyl-6-((2,2,2-trifluoroethoxy)methyl)pyrimidin-4-yl)ethanol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

1-(2-(3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-5-methyl-6-((2,2,2-trifluoroethoxy)methyl)pyrimidin-4-yl)ethanone (25 mg, 0.06 mmol) in dioxane (3 mL) and water (3 mL) was treated with sodium borohydride (8 mg, 0.22 mmol). The mixture was stirred at rt for 30 min. Acetic acid (0.5 mL) was added and the mixture was stirred for 25 min. The mixture was concentrated and the residue was purified by preparative HPLC to give the title compound as a dry film, 13 mg (48%).

Workup

  1. stirringthe mixture was stirred for 25 min
  2. concentrationThe mixture was concentrated
  3. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-68fb287020d94fff86e6d5794a8ce297
Source dataset
uspto-grants-2016_09
Patent number
US09439904B2

Reaction notes

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