Water → 4-chloro-6-(4-chloro-1H-imidazol-1-yl)pyrimidine

HRID 1876045Notes

Reaction equation

HRID 1876045 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[CH:4][N:3]=1.[Cl:9][C:10]1[N:11]=[CH:12][NH:13][CH:14]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[Cl:8][C:6]1[CH:7]=[C:2]([N:13]2[CH:14]=[C:10]([Cl:9])[N:11]=[CH:12]2)[N:3]=[CH:4][N:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 709434,6-DichloropyrimidineHCID 178478287HCID 178478287, compound

Product 1

HCID 592865734-chloro-6-(4-chloro-1H-imidazol-1-yl)pyrimidineYield 54.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4,6-dichloropyrimidine (1.8 g, 12 mmol), 4-chloro-1H-imidazole (1.23 g, 12.00 mmol), and cesium carbonate (3.91 g, 12.00 mmol) was stirred in DMF (8 mL) at room temperature for 18 h. The reaction was diluted into water and extracted with EtOAc. The combined organic layers were concentrated and purified by flash chromatography on a 120 g silica gel cartridge with 0 to 40% ethyl acetate in hexane to yield 4-chloro-6-(4-chloro-1H-imidazol-1-yl)pyrimidine (1.41 g, 54.6% yield). The positive identification of the 4-chloroimidazole regioisomer was accomplished by its NMR NOE properties. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.86 (1H, d, J=0.76 Hz), 8.33 (1H, d, J=1.51 Hz), 7.54 (1H, d, J=1.76 Hz), 7.30 (1H, d, J=0.76 Hz). LCMS: RT=0.81 min, MH+=215.1

Workup

  1. extractionextracted with EtOAc
  2. concentrationThe combined organic layers were concentrated
  3. custompurified by flash chromatography on a 120 g silica gel cartridge with 0 to 40% ethyl acetate in hexane

Sources & evidence

ORD record
ord-5b811ab84d00416b86edae677574b262
Source dataset
uspto-grants-2012_11
Patent number
US08309577B2

Reaction notes

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