Methyl iodide → HCID 11567585, compound

HRID 1173480Notes

Reaction equation

HRID 1173480 reaction equation
[H-].[Na+].[N:3]1[CH:8]=[CH:7][CH:6]=[N:5][C:4]=1[NH:9][CH2:10][CH2:11][N:12]([CH2:25][C:26]([F:29])([F:28])[F:27])[C:13]1[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[C:15]([C:21]([F:24])([F:23])[F:22])[CH:14]=1.I[CH3:31]>CN(C=O)C>[CH3:31][N:9]([C:4]1[N:5]=[CH:6][CH:7]=[CH:8][N:3]=1)[CH2:10][CH2:11][N:12]([CH2:25][C:26]([F:27])([F:28])[F:29])[C:13]1[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[C:15]([C:21]([F:23])([F:22])[F:24])[CH:14]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 11589176HCID 11589176, compound

Product 1

HCID 11567585HCID 11567585, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

NaH (60% in oil, 0.003 g, 0.075 mmol) was added to an ice-cold solution of 4-[[2-(pyrimidin-2-ylamino)ethyl](2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile (0.020 g, 0.051 mmol) in DMF (3 mL), under N2. After stirring for 5 min, iodomethane (0.011 g, 0.078 mmol) was added and stirred for 30 min. The mixture was partitioned between Et2O and water. The organic phase was washed with water and brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by silica gel chromatography (5-50% EtOAc/hexanes gradient) and the product crystallized from CH2Cl2/hexanes to give the title compound as a white solid (0.014 g, 68% yield): MS (ES) m/z 404 (M+1).

Workup

  1. stirringstirred for 30 min
  2. customThe mixture was partitioned between Et2O and water
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography (5-50% EtOAc/hexanes gradient)
  7. customthe product crystallized from CH2Cl2/hexanes

Sources & evidence

ORD record
ord-a07fa5e7b67049b69d1c90647a24c8f2
Source dataset
uspto-grants-2010_11
Patent number
US07834063B2

Reaction notes

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