Methanol → (2-(3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-6-((2,2,2-trifluoroethoxy)-methyl)pyrimidin-4-yl)(phenyl)methanol

HRID 59177Notes

Reaction equation

HRID 59177 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:15][C:16]2[N:21]=[C:20]([CH:22]=[O:23])[CH:19]=[C:18]([CH2:24][O:25][CH2:26][C:27]([F:30])([F:29])[F:28])[N:17]=2)[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]1.[C:31]1([Mg]Br)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.CO.[Cl-].[NH4+]>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:15][C:16]2[N:21]=[C:20]([CH:22]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[OH:23])[CH:19]=[C:18]([CH2:24][O:25][CH2:26][C:27]([F:29])([F:30])[F:28])[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 4

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 1178240362-(3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-6-((2,2,2-trifluoroethoxy)methyl)-pyrimidine-4-carbaldehydeHCID 178418255HCID 178418255, compound

Product 1

HCID 86344805(2-(3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-6-((2,2,2-trifluoroethoxy)-methyl)pyrimidin-4-yl)(phenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(3-Methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)-6-((2,2,2-trifluoroethoxy)methyl)-pyrimidine-4-carbaldehyde (0.10 g, 0.24 mmol) was dissolved in THF (5 mL). The mixture was cooled on an ice bath and phenylmagnesium bromide (3 M, 0.79 mL, 2.37 mmol) was added over 30 min. MeOH and ammonium chloride (aq, sat) were added. The mixture was extracted with EtOAc (×2). The organic phase was filtered through a pad of silica and sodium sulfate. The solvents were evaporated and the residue was purified by preparative HPLC to give the title compound as a dry film, 50 mg (22%).

Workup

  1. temperatureThe mixture was cooled on an ice bath
  2. extractionThe mixture was extracted with EtOAc (×2)
  3. filtrationThe organic phase was filtered through a pad of silica and sodium sulfate
  4. customThe solvents were evaporated
  5. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-60457fe987f943c69f77f2e6a214a4a7
Source dataset
uspto-grants-2016_09
Patent number
US09439904B2

Reaction notes

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