Imidazole → 4-Chloro-6-(1H-imidazol-1-yl)pyrimidine

HRID 581954Notes

Reaction equation

HRID 581954 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[NH:9]1[CH:13]=[CH:12][N:11]=[CH:10]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[Cl:8][C:6]1[CH:7]=[C:2]([N:9]2[CH:13]=[CH:12][N:11]=[CH:10]2)[N:3]=[CH:4][N:5]=1

Participants

6

Reactant 3

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 709434,6-Dichloropyrimidine

Product 1

HCID 27576124-Chloro-6-(1H-imidazol-1-yl)pyrimidineYield 67.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4,6-dichloropyrimidine (5 g, 33.56 mmol), imidazole (2.28 g, 33.56 mmol) and potassium carbonate (4.63 g, 33.56 mmol) in DMF (50 ml) is stirred at room temperature over night. The mixture is diluted with four volumes of water and extracted with dichloromethane. The organic extract is concentrated under reduced pressure and eluted through silica gel with a mixture of ethyl acetate and methanol (9:1). Evaporation of solvent and trituration of the residue with a mixture of diethyl ether and petroleum ether (1:1) leaves 15b (4.07 g, 67%). Mp 198-200° C.

Workup

  1. extractionextracted with dichloromethane
  2. extractionThe organic extract
  3. concentrationis concentrated under reduced pressure
  4. washeluted through silica gel with a mixture of ethyl acetate and methanol (9:1)
  5. customEvaporation of solvent and trituration of the residue
  6. additionwith a mixture of diethyl ether and petroleum ether (1:1)

Sources & evidence

ORD record
ord-d8e70efc20384575b75fc991697afd85
Source dataset
uspto-grants-1999_07
Patent number
US05922724

Reaction notes

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