2-(3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-6-((2,2,2-trifluoroethoxy)methyl)-pyrimidine-4-carbaldehyde → Cyclopropyl(2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-6-((2,2,2-trifluoroethoxy)methyl)pyrimidin-4-yl)methanol

HRID 59157Notes

Reaction equation

HRID 59157 reaction equation
[CH:1]1([Mg]Br)[CH2:3][CH2:2]1.[CH3:6][O:7][C:8]1[CH:9]=[C:10]([NH:20][C:21]2[N:26]=[C:25]([CH:27]=[O:28])[CH:24]=[C:23]([CH2:29][O:30][CH2:31][C:32]([F:35])([F:34])[F:33])[N:22]=2)[CH:11]=[CH:12][C:13]=1[N:14]1[CH:18]=[C:17]([CH3:19])[N:16]=[CH:15]1>C1COCC1>[CH:1]1([CH:27]([C:25]2[CH:24]=[C:23]([CH2:29][O:30][CH2:31][C:32]([F:33])([F:35])[F:34])[N:22]=[C:21]([NH:20][C:10]3[CH:11]=[CH:12][C:13]([N:14]4[CH:18]=[C:17]([CH3:19])[N:16]=[CH:15]4)=[C:8]([O:7][CH3:6])[CH:9]=3)[N:26]=2)[OH:28])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 1178240362-(3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-6-((2,2,2-trifluoroethoxy)methyl)-pyrimidine-4-carbaldehydeHCID 178418630HCID 178418630, compound

Product 1

HCID 86344616Cyclopropyl(2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-6-((2,2,2-trifluoroethoxy)methyl)pyrimidin-4-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To an ice-cold solution of cyclopropylmagnesium bromide (1.90 mL, 0.95 mmol) in THF (10 mL), a solution of 2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-6-((2,2,2-trifluoroethoxy)methyl)pyrimidine-4-carbaldehyde (40 mg, 0.09 mmol) in THF (6 mL) was added over 5 min. The mixture was stirred on ice-bath for 30 minutes before it was quenched with ammonium chloride (aq, sat). The solvent volume was reduced by evaporation. The mixture was extracted with dichloromethane, the organic phase was passed through a phase separator and concentrated in vacuum. The residue was purified by preparative HPLC to give the title compound as a dry film, 7 mg (16%).

Workup

  1. customwas quenched with ammonium chloride (aq, sat)
  2. customThe solvent volume was reduced by evaporation
  3. extractionThe mixture was extracted with dichloromethane
  4. concentrationconcentrated in vacuum
  5. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-f0147134e4364c48bd4999c5edf3e11c
Source dataset
uspto-grants-2016_09
Patent number
US09439904B2

Reaction notes

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