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

HRID 59173Notes

Reaction equation

HRID 59173 reaction equation
[CH2:1]([Mg]Br)[CH3:2].[CH3:5][O:6][C:7]1[CH:8]=[C:9]([NH:19][C:20]2[N:25]=[C:24]([C:26](=[O:28])[CH3:27])[CH:23]=[C:22]([CH2:29][O:30][CH2:31][C:32]([F:35])([F:34])[F:33])[N:21]=2)[CH:10]=[CH:11][C:12]=1[N:13]1[CH:17]=[C:16]([CH3:18])[N:15]=[CH:14]1.[Cl-].[NH4+]>C1COCC1>[CH3:5][O:6][C:7]1[CH:8]=[C:9]([NH:19][C:20]2[N:25]=[C:24]([C:26]([OH:28])([CH2:1][CH3:2])[CH3:27])[CH:23]=[C:22]([CH2:29][O:30][CH2:31][C:32]([F:33])([F:34])[F:35])[N:21]=2)[CH:10]=[CH:11][C:12]=1[N:13]1[CH:17]=[C:16]([CH3:18])[N:15]=[CH:14]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 178418443HCID 178418443, compound2×

Product 1

HCID 863449842-(2-(3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-6-((2,2,2-trifluoroethoxy)-methyl)pyrimidin-4-yl)butan-2-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Ethylmagnesium bromide (0.86 mL, 2.57 mmol, 3M in THF) was dissolved in THF (5 mL). 1-(2-(3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-6-((2,2,2-trifluoroethoxy)methyl)-pyrimidin-4-yl)ethanone (140 mg, 0.32 mmol) was dissolved in THF (5 mL) and was added slowly to the solution of ethylmagnesium bromide. The mixture was cooled on ice, ammonium chloride (sat, aq, 5 mL) was added and the mixture was stirred for 5 min. The mixture was extracted with EtOAc (×2). The solvents were evaporated and the residue was purified by column chromatography on silica eluting with a gradient of MeOH in DCM to give the title compound as an oil, 63 mg (42%).

Workup

  1. additionwas added
  2. extractionThe mixture was extracted with EtOAc (×2)
  3. customThe solvents were evaporated
  4. customthe residue was purified by column chromatography on silica eluting with a gradient of MeOH in DCM

Sources & evidence

ORD record
ord-260dd5149c6140c3a68958ef320c9116
Source dataset
uspto-grants-2016_09
Patent number
US09439904B2

Reaction notes

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