Water → 4-[5-Acetyl-3,6-dimethyl-2-oxo-1-(3-trifluoromethyl-phenyl)-1,2,3,4-tetrahydro-pyrimidin-4-yl]-3-bromo-benzonitrile

HRID 927000Notes

Reaction equation

HRID 927000 reaction equation
CI.[C:3]([C:6]1[CH:7]([C:24]2[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[CH:26][C:25]=2[Br:32])[NH:8][C:9](=[O:23])[N:10]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)[C:11]=1[CH3:12])(=[O:5])[CH3:4].[C:33](=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O.C(OCC)(=O)C>[C:3]([C:6]1[CH:7]([C:24]2[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[CH:26][C:25]=2[Br:32])[N:8]([CH3:33])[C:9](=[O:23])[N:10]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:20])([F:21])[F:22])[CH:14]=2)[C:11]=1[CH3:12])(=[O:5])[CH3:4]

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 1186916954-[5-Acetyl-6-methyl-2-oxo-1-(3-trifluoromethyl-phenyl)-1,2,3,4-tetrahydro-pyrimidin-4-yl]-3-bromo-benzonitrile2×

Product 1

HCID 1186916864-[5-Acetyl-3,6-dimethyl-2-oxo-1-(3-trifluoromethyl-phenyl)-1,2,3,4-tetrahydro-pyrimidin-4-yl]-3-bromo-benzonitrile

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methyliodide (c=2 mol/L, 3.24 mL, 6.48 mmol) is added to a suspension of 4-[5-acetyl-6-methyl-2-oxo-1-(3-trifluoromethyl-phenyl)-1,2,3,4-tetrahydro-pyrimidin-4-yl]-3-bromo-benzonitrile (intermediate 3) (2.48 g, 5.18 mmol) and cesium carbonate (2.20 g, 6.74 mmol) in N,N-dimethylformamide (50.0 mL). The reaction mixture is stirred at room temperature overnight. Water and ethyl acetate are added and the phases are separated. The aqueous phase is extracted twice with ethyl acetate and the combined organic phases are washed with saturated sodium chloride solution, dried over MgSO4 and concentrated. The residue is purified by reversed phase HPLC. Yield: 2.64 g. ESI mass spectrum: [(79Br)-M+H]+=492, [(81Br)-M+H]+=494; Retention time HPLC: 1.06 min (HPLC method Z018_S04).

Workup

  1. customthe phases are separated
  2. extractionThe aqueous phase is extracted twice with ethyl acetate
  3. washthe combined organic phases are washed with saturated sodium chloride solution
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue is purified by reversed phase HPLC
  7. custom1.06 min (HPLC method Z018_S04)

Sources & evidence

ORD record
ord-8c66ffed68eb4dadbf98ec6170148b0b
Source dataset
uspto-grants-2016_03
Patent number
US09290457B2

Reaction notes

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