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

HRID 59160Notes

Reaction equation

HRID 59160 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:16][C:17]2[N:22]=[C:21]([C:23](=[O:25])[CH3:24])[CH:20]=[C:19]([CH2:26][O:27][CH2:28][C:29]([F:32])([F:31])[F:30])[N:18]=2)[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([O:14][CH3:15])[N:11]=[CH:10]1.O1CCOC[CH2:34]1.C[Mg]Br.[Cl-].[NH4+]>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:16][C:17]2[N:22]=[C:21]([C:23]([OH:25])([CH3:34])[CH3:24])[CH:20]=[C:19]([CH2:26][O:27][CH2:28][C:29]([F:30])([F:31])[F:32])[N:18]=2)[CH:6]=[CH:7][C:8]=1[N:9]1[CH:13]=[C:12]([O:14][CH3:15])[N:11]=[CH:10]1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 312751,4-DioxaneHCID 117823955HCID 117823955, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 863446132-(2-(3-Methoxy-4-(4-methoxy-1H-imidazol-1-yl)phenylamino)-6-((2,2,2-trifluoroethoxy)-methyl)pyrimidin-4-yl)propan-2-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1-(2-(3-Methoxy-4-(4-methoxy-1H-imidazol-1-yl)phenylamino)-6-((2,2,2-trifluoroethoxy)-methyl)pyrimidin-4-yl)ethanone (145 mg, 0.32 mmol) was coevaporated with dioxane and dissolved in THF (10 mL). The mixture was added slowly to a well stirred solution of methylmagnesium bromide (0.857 mL, 3 M solution, 2.57 mmol) in THF (5 mL). The mixture was stirred at rt for 5 min. The mixture was cooled on ice bath and ammonium chloride (aq, 5 mL) was added. The mixture was extracted with ethyl acetate (2×10 mL), the organic phase was filtered and concentrated in vacuum. The residue was separated purified by preparative HPLC to give the title compound as a dry film, 68 mg (46%).

Workup

  1. additionThe mixture was added slowly to a well
  2. temperatureThe mixture was cooled on ice bath
  3. extractionThe mixture was extracted with ethyl acetate (2×10 mL)
  4. filtrationthe organic phase was filtered
  5. concentrationconcentrated in vacuum
  6. customThe residue was separated
  7. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-f3ec5e66af764f05a95c451b4cdeaf06
Source dataset
uspto-grants-2016_09
Patent number
US09439904B2

Reaction notes

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