Methyl iodide → Pyrimidine, 2,4-dichloro-6-(1-methyl-1H-imidazol-2-yl)-

HRID 896234Notes

Reaction equation

HRID 896234 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]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 22324126HCID 22324126, compound

Product 1

HCID 22349975Pyrimidine, 2,4-dichloro-6-(1-methyl-1H-imidazol-2-yl)-Yield 58.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

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.

Workup

  1. temperaturewas refluxed for 48 h
  2. customthe solvent was evaporated
  3. customthe residue was partitioned between water and CH2Cl2
  4. washThe CH2Cl2 layer was washed successively with water and brine
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-322bf7a1afed45a7abb526dafd75b8cd
Source dataset
uspto-grants-2005_07
Patent number
US06919347B2

Reaction notes

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