Water → HCID 58485290, compound

HRID 1046092Notes

Reaction equation

HRID 1046092 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5](Cl)=[N:6][CH:7]=1.[CH3:9][C:10]1[NH:11][CH:12]=[C:13]([CH3:15])[N:14]=1.C([O-])([O-])=O.[K+].[K+].O>CN1C(=O)CCC1.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[N:4][C:5]([N:11]2[CH:12]=[C:13]([CH3:15])[N:14]=[C:10]2[CH3:9])=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 6066655-Bromo-2-chloropyrimidineHCID 178430880HCID 178430880, compound

Product 1

HCID 58485290HCID 58485290, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-bromo-2-chloropyrimidine (0.3 g, 1.55 mmol) in NMP (15 mL) were added 2,4-dimethyl-1H-imidazole (0.224 g, 2.2 mmol) and K2CO3 (0.43 g, 3.1 mmol). The resulting solution was stirred at 80° C. overnight. After water (50 mL) and EtOAc (50 mL) were added, the mixture was extracted with EtOAc (3×50 mL). The combined organic layer was washed with brine (50 mL), dried over Na2SO4, filtered, and concentrated. The residue was purified by pre-TLC to afford 5-bromo-2-(2,4-dimethyl-1H-imidazol-1-yl)-pyrimidine (0.2 g, 51%).

Workup

  1. extractionthe mixture was extracted with EtOAc (3×50 mL)
  2. washThe combined organic layer was washed with brine (50 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by pre-TLC

Sources & evidence

ORD record
ord-de455369368442f9a098e8aa327cf971
Source dataset
uspto-grants-2013_10
Patent number
US08569292B2

Reaction notes

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