Potassium Hydroxide → 8-Morpholinoimidazo[1,2-a]pyrazine

HRID 1086170Notes

Reaction equation

HRID 1086170 reaction equation
Br[C:2]1[N:3]=[C:4]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[CH:7]=1.[OH-].[K+]>[Pd].CO>[O:14]1[CH2:13][CH2:12][N:11]([C:4]2[C:5]3[N:6]([CH:8]=[CH:9][N:10]=3)[CH:7]=[CH:2][N:3]=2)[CH2:16][CH2:15]1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 100394454-(6-Bromoimidazo[1,2-a]pyrazin-8-yl)morpholine

Product 1

HCID 118202328-Morpholinoimidazo[1,2-a]pyrazineYield 94.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

200 mg of palladium on charcoal (10% palladium) are added to a solution containing 0.5 g (1.77 mmol) of 6-bromo-8-morpholinoimidazo[1,2-a]pyrazine for 120 ml of anhydrous methanol and 2 g of potassium hydroxide. The mixture is hydrogenated at atmospheric pressure for 12 hours. The solution is filtered, concentrated and taken up with water; after extraction with dichloromethane and evaporation of the solvent, 0.34 g (92%) of 8-morpholinoimidazo[1,2-a]pyrazine (m.p. 127° C.) is obtained.

Workup

  1. filtrationThe solution is filtered
  2. concentrationconcentrated
  3. extractionafter extraction
  4. customwith dichloromethane and evaporation of the solvent

Sources & evidence

ORD record
ord-6874bc8fc2c1412ebf0e4861a522d0ba
Source dataset
uspto-grants-1991_07
Patent number
US05028605

Reaction notes

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