Ammonium Chloride → 2-(2-(3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-6-((2,2,2-trifluoroethoxy)-methyl)pyrimidin-4-yl)propan-2-ol

HRID 59145Notes

Reaction equation

HRID 59145 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]([CH2:25][O:26][CH2:27][C:28]([F:31])([F:30])[F:29])[N:17]=2)[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1.[CH3:32][Mg]Br.[Cl-].[NH4+]>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:15][C:16]2[N:21]=[C:20]([C:22]([OH:24])([CH3:32])[CH3:23])[CH:19]=[C:18]([CH2:25][O:26][CH2:27][C:28]([F:29])([F:30])[F:31])[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 25517Ammonium ChlorideHCID 1178240761-(2-(3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-6-((2,2,2-trifluoroethoxy)-methyl)pyrimidin-4-yl)ethanoneHCID 178418573HCID 178418573, compound

Product 1

HCID 863440682-(2-(3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-6-((2,2,2-trifluoroethoxy)-methyl)pyrimidin-4-yl)propan-2-olYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1-(2-(3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-6-((2,2,2-trifluoroethoxy)-methyl)pyrimidin-4-yl)ethanone (178 mg, 0.41 mmol) was dissolved in THF (5 mL). The mixture was added to methylmagnesium bromide (3 M in THF, 1.090 mL, 3.27 mmol) in THF (5 mL). The mixture was stirred at rt for 5 min. The mixture was cooled at 0° C. and ammonium chloride (aq) was added. The mixture was extracted by EtOAc, the organic phase was dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica eluting with a gradient of methanol in DCM to give the title compound as a solid 107 mg (58%).

Workup

  1. temperatureThe mixture was cooled at 0° C.
  2. extractionThe mixture was extracted by EtOAc
  3. dry with materialthe organic phase was dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica eluting with a gradient of methanol in DCM

Sources & evidence

ORD record
ord-693c2d6f755c43819172bf378225c1fc
Source dataset
uspto-grants-2016_09
Patent number
US09439904B2

Reaction notes

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