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

HRID 59175Notes

Reaction equation

HRID 59175 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[C:9]1[CH:14]=[C:13]([CH3:15])[N:12]=[N:11][CH:10]=1.[CH3:33][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])([CH3:33])[CH3:24])[CH:20]=[C:19]([CH2:26][O:27][CH2:28][C:29]([F:30])([F:32])[F:31])[N:18]=2)[CH:6]=[CH:7][C:8]=1[C:9]1[CH:14]=[C:13]([CH3:15])[N:12]=[N:11][CH:10]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 1178212521-(2-(3-Methoxy-4-(6-methylpyridazin-4-yl)phenylamino)-6-((2,2,2-trifluoroethoxy)-methyl)pyrimidin-4-yl)ethanoneHCID 178418573HCID 178418573, compound

Product 1

HCID 863449822-(2-(3-Methoxy-4-(6-methylpyridazin-4-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-(6-methylpyridazin-4-yl)phenylamino)-6-((2,2,2-trifluoroethoxy)methyl)-pyrimidin-4-yl)ethanone (60 mg, 0.13 mmol) was dissolved in THF (5 mL) and was added slowly to a solution of methylmagnesium bromide (3 M in THF, 0.358 mL, 1.07 mmol) in THF (5 mL). The mixture was stirred for 5 min. The mixture was cooled on an ice bath and ammonium chloride (sat, aq, 5 mL) was added. 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 a solid, 42 mg (68%).

Workup

  1. temperatureThe mixture was cooled on an ice bath
  2. stirringThe mixture was stirred for 5 min
  3. extractionThe mixture was extracted with EtOAc (×2)
  4. customThe solvents were evaporated
  5. customthe residue was purified by column chromatography on silica eluting with a gradient of MeOH in DCM

Sources & evidence

ORD record
ord-2a7e90e9a9524db698cacd60d51fcff4
Source dataset
uspto-grants-2016_09
Patent number
US09439904B2

Reaction notes

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