Sodium Chloride → HCID 11774169, compound

HRID 2112604Notes

Reaction equation

HRID 2112604 reaction equation
Cl[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]([Cl:17])[N:5]=[C:4]([N:18]2[CH:22]=[CH:21][N:20]=[CH:19]2)[N:3]=1.[F:23][C:24]([F:28])([F:27])[CH2:25][NH2:26].[Cl-].[Na+]>CN(C)C=O>[Cl:17][C:6]1[N:5]=[C:4]([N:18]2[CH:22]=[CH:21][N:20]=[CH:19]2)[N:3]=[C:2]([NH:26][CH2:25][C:24]([F:28])([F:27])[F:23])[C:7]=1[C:8]1[C:13]([F:14])=[CH:12][C:11]([F:15])=[CH:10][C:9]=1[F:16]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 9773Ethanamine, 2,2,2-trifluoro-HCID 86041445HCID 86041445, compound

Product 1

HCID 11774169HCID 11774169, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4,6-dichloro-2-(1H-imidazol-1-yl)-5-(2,4,6-trifluorophenyl)pyrimidine (35 mg, 0.10 mmol) and 2,2,2-trifluoroethylamine (50 mg, 0.5 mmol) in 2 mL of N,N-dimethylformamide is stirred at room temperature for 1 h. A saturated sodium chloride solution is added, and the product is extracted with ehtyl acetate. The organic solution is washed with saturated sodium chloride (×4), dried over magnesium sulfate, and concentrated. The residue is chromatographed over silica gel, eluting with a gradient of 20% ethyl acetate in hexanes to 50% ethyl acetate in hexanes. Concentration provides 6-chloro-2-(1H-imidazol-1-yl)-N-(2,2,2-trifluoroethyl)-5-(2,4,6-trifluorophenyl)pyrimidin-4-amine as a light tan solid (36 mg, mp 168-170° C.). MS: m/z 408.2 (M+H).

Workup

  1. extractionthe product is extracted with ehtyl acetate
  2. washThe organic solution is washed with saturated sodium chloride (×4)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue is chromatographed over silica gel
  6. washeluting with a gradient of 20% ethyl acetate in hexanes to 50% ethyl acetate in hexanes
  7. concentrationConcentration

Sources & evidence

ORD record
ord-6bdad1b7c7b144b8bbb3e63081b3168e
Source dataset
uspto-grants-2009_04
Patent number
US07524849B2

Reaction notes

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