Methyl iodide → HCID 11361437, compound

HRID 2112597Notes

Reaction equation

HRID 2112597 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[C:13]([F:14])=[CH:12][C:11]([F:15])=[CH:10][C:9]=2[F:16])=[C:6]([NH:17][CH2:18][C:19]([F:22])([F:21])[F:20])[N:5]2[N:23]=[CH:24][N:25]=[C:4]2[N:3]=1.I[CH3:27].[H-].[Na+]>CS(C)=O.C(OCC)(=O)C>[Cl:1][C:2]1[N:3]=[C:4]2[N:25]([CH3:27])[CH:24]=[N:23][N:5]2[C:6](=[N:17][CH2:18][C:19]([F:21])([F:20])[F:22])[C:7]=1[C:8]1[C:13]([F:14])=[CH:12][C:11]([F:15])=[CH:10][C:9]=1[F:16]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 11188211HCID 11188211, compound

Product 1

HCID 11361437HCID 11361437, compoundYield 24.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-chloro-6-(2,4,6-trifluorophenyl)-N-(2,2,2-trifluoroethyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-amine (300 mg, 0.78 mmol) in 4 mL of dimethylsulfoxide at room temperature is added iodomethane (146 μL, 2.34 mmol) followed by sodium hydride (60% in mineral oil, 31 mg, 0.78 mmol). The mixture is then stirred at room temperature for 18 h, and diluted with ethyl acetate. The organic layer is washed with water and saturated sodium chloride, dried over magnesium sulfate, and concentrated. The residue is chromatographed over silica gel, eluting with 20% ethyl acetate in hexanes. Concentration provides N-[5-chloro-3-methyl-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]pyrimidin-7(3H)-ylidene]-2,2,2-trifluoroethanamine as a white solid (76 mg). MS: m/z 396.0 (M+H).

Workup

  1. washThe organic layer is washed with water and saturated sodium chloride
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue is chromatographed over silica gel
  5. washeluting with 20% ethyl acetate in hexanes
  6. concentrationConcentration

Sources & evidence

ORD record
ord-df0867f383194f619a92322245da08b7
Source dataset
uspto-grants-2009_04
Patent number
US07524849B2

Reaction notes

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