4,6-Dichloropyrimidine → 4-Chloro-6-(2-chloro-imidazol-1-yl)-pyrimidine

HRID 19499Notes

Reaction equation

HRID 19499 reaction equation
[Cl:1][C:2]1[NH:3][CH:4]=[CH:5][N:6]=1.[Cl:7][C:8]1[CH:13]=[C:12](Cl)[N:11]=[CH:10][N:9]=1.CCN(C(C)C)C(C)C>C(O)CCC>[Cl:7][C:8]1[CH:13]=[C:12]([N:3]2[CH:4]=[CH:5][N:6]=[C:2]2[Cl:1])[N:11]=[CH:10][N:9]=1

Participants

5

Reactant 3

HCID 709434,6-DichloropyrimidineHCID 81531DiisopropylethylamineHCID 27733282-chloro-1H-imidazole

Product 1

HCID 589730674-Chloro-6-(2-chloro-imidazol-1-yl)-pyrimidineYield 62%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
120 °C

Procedure

2-Chloro-1H-imidazole (2.0 g, 20 mmol), 4,6-dichloropyrimidine (6 g, 40 mmol) and DIEA (10.4 ml, 60 mmol) were mixed in 40 mL butanol and refluxed at 120° C. for 24 hours. The solvent was removed by rotary evaporation. The crude product was purified by flash chromatography on silica gel (0% EtOAc/hexanes to 20% EtOAc/hexanes gradient), afforded the title compound (2.6 g, 62% yield) as yellow solid. Rf=0.25 (20% EtOAc/hexanes); 1H NMR 400 MHz (DMSO-d6) δ 9.13 (s, 1H), 8.17 (s, 1H), 7.94 (d, 1H), 7.17 (d, 1 H); MS m/z 215.4 (M+1).

Workup

  1. customThe solvent was removed by rotary evaporation
  2. customThe crude product was purified by flash chromatography on silica gel (0% EtOAc/hexanes to 20% EtOAc/hexanes gradient)

Sources & evidence

ORD record
ord-cca4f24e3a8d47dda38e49c5c9c0f98e
Source dataset
uspto-grants-2010_06
Patent number
US07745437B2

Reaction notes

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