Methyl iodide → 2,4-Dichloro-6-(1-methylimidazole-2-yl)pyrimidine
Reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4]([C:9]2[NH:10][CH:11]=[CH:12][N:13]=2)[N:3]=1.[C:14]([O-])([O-])=O.[K+].[K+].CI>CC(C)=O>[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4]([C:9]2[N:13]([CH3:14])[CH:12]=[CH:11][N:10]=2)[N:3]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 2,4-Dichloro-6-(1-dimethylsulfamoylimidazole-2-yl)pyrimidine 83 (246 mg, 0.76 mmol) in 10 mL of 1.5 N HCl was refluxed for 1 h. After cooling to RT, the pH was adjusted to 8.5 with aq NaHCO3 and the product was extracted into CH2Cl2. After drying the CH2Cl2 layer was evaporated to give 110 mg of 2,4-dichloro-6-(imidazole-2-yl)pyrimidine. A mixture of 2,4-dichloro-6-(imidazole-2-yl)pyrimidine (121 mg, 0.56 mmol), K2CO3 (100 mg, 0.72 mmol) and CH3I (2.280 g, 1 mL, 16 mmol) in 15 mL of dry acetone was refluxed for 48 h. After cooling to RT, the solvent was evaporated and the residue was partitioned between water and CH2Cl2. The CH2Cl2 layer was washed successively with water and brine, and then the solvent was evaporated to give 75 mg of 2,4-dichloro-6-(1-methylimidazole-2-yl)pyrimidine 86.