Water → 4-(5-Bromo-imidazol-1-yl)-2-chloro-pyrimidine

HRID 1784384Notes

Reaction equation

HRID 1784384 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[Br:15][C:16]1[NH:20][CH:19]=[N:18][CH:17]=1.O>CN(C=O)C>[Br:15][C:16]1[N:20]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=2)[CH:19]=[N:18][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 775312,4-DichloropyrimidineHCID 961251H-Imidazole, 4-bromo-

Product 1

HCID 575925314-(5-Bromo-imidazol-1-yl)-2-chloro-pyrimidineYield 23.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 2,4-dichloropyrimidine (0.447 g, 3 mmol) in anhydrous DMF (4 ml) was added potassium carbonate (0.415 g, 3 mmol). The reaction mixture was cooled (0° C.) under an inert atmosphere before the addition of 5-bromo-1-H-imidazole (0.441 g, 3 mmol) as solution in DMF (2 ml). The reaction was then allowed to stir at this temperature for a further 3 hours whereupon water (3 ml) was added. The resultant white precipitate was removed from the mixture by filtration and washed with water before being dried to give the title compound as a white solid (0.18 g, 23%) which was suitably pure to be used without further purification. m/z (LC-MSW, ESP):259.2,261.2 (bromine isotopes) [M+H]+, R/T=3.47 mins.

Workup

  1. additionwas added
  2. customThe resultant white precipitate was removed from the mixture by filtration
  3. washwashed with water
  4. custombefore being dried

Sources & evidence

ORD record
ord-0c6491ea44794e49912abacafa2be741
Source dataset
uspto-grants-2009_03
Patent number
US07504397B2

Reaction notes

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