Sodium hydride → 2,3-Dimethyl-8-(2,6-dimethylbenzyloxy)imidazo[1,2-a]pyrazine

HRID 1058571Notes

Reaction equation

HRID 1058571 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[C:5]=1[CH2:6][OH:7].Cl[C:14]1[C:15]2[N:16]([C:20]([CH3:24])=[C:21]([CH3:23])[N:22]=2)[CH:17]=[CH:18][N:19]=1>C(#N)C>[CH3:23][C:21]1[N:22]=[C:15]2[C:14]([O:7][CH2:6][C:5]3[C:8]([CH3:12])=[CH:9][CH:10]=[CH:11][C:4]=3[CH3:3])=[N:19][CH:18]=[CH:17][N:16]2[C:20]=1[CH3:24]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 186748(2,6-Dimethylphenyl)methanolHCID 107499238-Chloro-2,3-dimethylimidazo[1,2-a]pyrazine

Product 1

HCID 99038552,3-Dimethyl-8-(2,6-dimethylbenzyloxy)imidazo[1,2-a]pyrazineYield 50%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Sodium hydride (0.15 g, 3 mmol) (50% in oil) was added to a stirred solution of 2,6-dimethylbenzylalcohol in acetonitril (10 ml). 8-chloro-2,3-dimethylimidazo[1,2-a]pyrazine (0.4 g, 3 mmol) was added and the reaction mixture was refluxed for 20 h. The solvent was evaporated under reduced pressure and the residue was solved in methylene chloride and washed with water. The organic layer was evaporated under reduced pressure and the residue was purified by column chromatography on silica gel using ethylacetate:petroleum ether(40-60) 1:1 as eluent. Crystallization from petroleum ether gave 0.42 g (50%) of the title compound.

Workup

  1. temperaturethe reaction mixture was refluxed for 20 h
  2. customThe solvent was evaporated under reduced pressure
  3. washwashed with water
  4. customThe organic layer was evaporated under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel
  6. customCrystallization from petroleum ether

Sources & evidence

ORD record
ord-6dadd8d37f48432a8dc1e428596493c5
Source dataset
uspto-grants-2003_02
Patent number
US06518270B1

Reaction notes

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