HCID 117823909, compound → 2-(6-(((3,3-Difluorocyclobutyl)methoxy)methyl)-2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)pyrimidin-4-yl)propan-2-ol

HRID 59147Notes

Reaction equation

HRID 59147 reaction equation
[CH3:1][Mg]Br.[F:4][C:5]1([F:36])[CH2:8][CH:7]([CH2:9][O:10][CH2:11][C:12]2[N:17]=[C:16]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([N:25]4[CH:29]=[C:28]([CH3:30])[N:27]=[CH:26]4)=[C:21]([O:31][CH3:32])[CH:20]=3)[N:15]=[C:14]([C:33](=[O:35])[CH3:34])[CH:13]=2)[CH2:6]1>O1CCCC1>[F:36][C:5]1([F:4])[CH2:8][CH:7]([CH2:9][O:10][CH2:11][C:12]2[N:17]=[C:16]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([N:25]4[CH:29]=[C:28]([CH3:30])[N:27]=[CH:26]4)=[C:21]([O:31][CH3:32])[CH:20]=3)[N:15]=[C:14]([C:33]([OH:35])([CH3:1])[CH3:34])[CH:13]=2)[CH2:6]1

Participants

4

Reactant 2

HCID 117823909HCID 117823909, compoundHCID 178418573HCID 178418573, compound2×

Product 1

HCID 863440672-(6-(((3,3-Difluorocyclobutyl)methoxy)methyl)-2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)phenylamino)pyrimidin-4-yl)propan-2-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methylmagnesium bromide (0.105 mL, 0.31 mmol) was added to an ice-cold solution of 1-(6-(((3,3-difluorocyclobutyl)methoxy)methyl)-2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)-phenylamino)pyrimidin-4-yl)ethanone (16 mg, 0.03 mmol) in tetrahydrofuran (5 mL) under argon atmosphere. The mixture was stirred for 10 min. Methylmagnesium bromide (0.058 mL, 0.17 mmol) was added and the mixture was stirred for 10 minutes. The reaction was quenched with of ammonium chloride (aq, sat). The mixture was concentrated. The residue was extracted with dichloromethane. The organic phase was dried over sodium sulfate and concentrated. The residue was purified by preparative HPLC to give the title compound as a dry film (4 mg, 24%).

Workup

  1. stirringthe mixture was stirred for 10 minutes
  2. customThe reaction was quenched with of ammonium chloride (aq, sat)
  3. concentrationThe mixture was concentrated
  4. extractionThe residue was extracted with dichloromethane
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-92980f0133234621864836908c941844
Source dataset
uspto-grants-2016_09
Patent number
US09439904B2

Reaction notes

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