Methyl iodide → HCID 22452600, compound

HRID 2185839Notes

Reaction equation

HRID 2185839 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7]([C:9]2[CH:10]=[C:11]([C:26]#[N:27])[C:12](=[O:25])[NH:13][C:14]=2[C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=2)[CH:6]=[CH:5][N:4]=1.[C:28](=O)([O-])[O-].[Cs+].[Cs+].CI>CN(C=O)C>[CH3:28][N:13]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=2)=[C:9]([C:7]2[CH:6]=[CH:5][N:4]=[C:3]([S:2][CH3:1])[N:8]=2)[CH:10]=[C:11]([C:26]#[N:27])[C:12]1=[O:25]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 22452602HCID 22452602, compound

Product 1

HCID 22452600HCID 22452600, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-(2-methylsulfanylpyrimidin-4-yl)-2-oxo-6-(3-trifluoromethylphenyl)-1,2-dihydropyridine-3-carbonitrile (150 mg, 0.00040 mol) in 3 mL DMF was added cesium carbonate (200 mg, 0.00060 mol) and methyl iodide (1 mL, 0.0154 mol) and the solution stirred at room temperature for 1 h. The mixture was the partitioned between H2O and EtOAc and the organic phase dried over anhydrous sodium sulfate and concentrated. Chromatography on silica with 3% MeOH in CH2Cl2 yields 100 mg (65%) 1-methyl-5-(2-methylsulfanyl-pyrimidin-4-yl)-2-oxo-6-(3-trifluoromethyl-phenyl)-1,2-dihydropyridine-3-carbonitrile as a solid.

Workup

  1. custompartitioned between H2O and EtOAc
  2. dry with materialthe organic phase dried over anhydrous sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-821b55437c0e4e19aece4987187b3eca
Source dataset
uspto-grants-2002_06
Patent number
US06403596B1

Reaction notes

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