Sodium hydride → 4-Chloro-6-[(2,2,2-trifluoroethyl)amino]-5-(2,4,6-trifluorophenyl)pyrimidin-2-yl(methyl)cyanamide

HRID 2112598Notes

Reaction equation

HRID 2112598 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]2[N:25]([CH3:26])[CH:24]=[N:23][N:5]2[C:6](=[N:17][CH2:18][C:19]([F:22])([F:21])[F:20])[C:7]=1[C:8]1[C:13]([F:14])=[CH:12][C:11]([F:15])=[CH:10][C:9]=1[F:16].[H-].[Na+]>CS(C)=O.C(OCC)(=O)C>[Cl:1][C:2]1[C:7]([C:8]2[C:9]([F:16])=[CH:10][C:11]([F:15])=[CH:12][C:13]=2[F:14])=[C:6]([NH:17][CH2:18][C:19]([F:21])([F:22])[F:20])[N:5]=[C:4]([N:25]([CH3:26])[C:24]#[N:23])[N:3]=1

Participants

5

Reactant 2

HCID 24758Sodium hydrideHCID 11361437HCID 11361437, compound

Product 1

HCID 113953414-Chloro-6-[(2,2,2-trifluoroethyl)amino]-5-(2,4,6-trifluorophenyl)pyrimidin-2-yl(methyl)cyanamideYield 45.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 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 (345 mg, 0.87 mmol) in 1 mL of dimethylsulfoxide at room temperature is added sodium hydride (60% in mineral oil, 35 mg, 0.87 mmol). The mixture is then stirred at room temperature for 2 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 10% ethyl acetate in hexanes. Concentration provides 4-chloro-6-[(2,2,2-trifluoroethyl)amino]-5-(2,4,6-trifluorophenyl)pyrimidin-2-yl(methyl)cyanamide as a white solid (157 mg). MS: m/z 396.1 (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 10% ethyl acetate in hexanes
  6. concentrationConcentration

Sources & evidence

ORD record
ord-79a2b2806cda45468d8c087ce097f8a2
Source dataset
uspto-grants-2009_04
Patent number
US07524849B2

Reaction notes

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