Imidazole → HCID 86041445, compound

HRID 2112603Notes

Reaction equation

HRID 2112603 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[C:5]([C:9]2[C:14]([F:15])=[CH:13][C:12]([F:16])=[CH:11][C:10]=2[F:17])=[C:4]([Cl:18])[N:3]=1.[NH:19]1[CH:23]=[CH:22][N:21]=[CH:20]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:18][C:4]1[C:5]([C:9]2[C:14]([F:15])=[CH:13][C:12]([F:16])=[CH:11][C:10]=2[F:17])=[C:6]([Cl:8])[N:7]=[C:2]([N:19]2[CH:23]=[CH:22][N:21]=[CH:20]2)[N:3]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 86041448HCID 86041448, compound

Product 1

HCID 86041445HCID 86041445, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the above 2,4,6-trichloro-5-(2,4,6-trifluorophenyl)pyrimidine (104 mg), imidazole (23 mg, 0.33 mmol), and potassium carbonate (92 mg, 0.66 mmol) in 2 mL of N,N-dimethylformamide is stirred at room temperature for 3 h. The mixture is partitioned between ethyl acetate and saturated sodium chloride. The organic layer 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 hexanes to 50% ethyl acetate in hexanes. Concentration provides 4,6-dichloro-2-(1H-imidazol-1-yl)-5-(2,4,6-trifluorophenyl)pyrimidine as a tan solid (71 mg, mp 72-74° C.). MS: m/z 345.2 (M+H).

Workup

  1. customThe mixture is partitioned between ethyl acetate and saturated sodium chloride
  2. washThe organic layer 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 hexanes to 50% ethyl acetate in hexanes
  7. concentrationConcentration

Sources & evidence

ORD record
ord-6e591ed453a448b58146b3fd9f454ed1
Source dataset
uspto-grants-2009_04
Patent number
US07524849B2

Reaction notes

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