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

HRID 1646209Notes

Reaction equation

HRID 1646209 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[CH:4]1.[Cl:8][C:9]1[CH:14]=[C:13](Cl)[N:12]=[CH:11][N:10]=1.O>CN(C=O)C>[Cl:8][C:9]1[CH:14]=[C:13]([N:3]2[CH:7]=[CH:6][N:5]=[CH:4]2)[N:12]=[CH:11][N:10]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 24758Sodium hydrideHCID 709434,6-Dichloropyrimidine

Product 1

HCID 27576124-Chloro-6-(1H-imidazol-1-yl)pyrimidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a stirred suspension of sodium hydride (0.65g, 55% dispersion in oil, pre-washed with petrol) in dry DMF (5ml) at 10-15° C under nitrogen, was added a solution of imidazole (1.02g, 15 mmol) over five minutes. The reaction mixture effervesced and an exotherm took place. After stirring for 11/2hours at room temperature, the cloudy solution was added drop-wise over one hour to a solution of 4,6-dichloropyrimidine in dry DMF (10ml) at 0° C. for one hour, added to water and then extracted with ether (×3). The combined ether extracts were washed with dilute sodium hydroxide solution and water (×3) and then dried. Concentration under reduced pressure gave 4-chloro-6-(imidazol-1-yl)pyrimidine as a pale yellow solid (1.00g); m.p. 122-4° C., which was used without further purification.

Workup

  1. extractionextracted with ether (×3)
  2. washThe combined ether extracts were washed with dilute sodium hydroxide solution and water (×3)
  3. customdried
  4. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-7713b13d1b264f5c86f94179fa01cc6e
Source dataset
uspto-grants-1993_01
Patent number
US05179098

Reaction notes

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