Imidazo(1,2-a)pyrazin-8-amine, 3-bromo-N-methyl- → N-Methylimidazo[1,2-A]pyrazin-8-amine

HRID 457017Notes

Reaction equation

HRID 457017 reaction equation
Br[C:2]1[N:6]2[CH:7]=[CH:8][N:9]=[C:10]([NH:11][CH3:12])[C:5]2=[N:4][CH:3]=1>CO.[Pd]>[N:4]1[CH:3]=[CH:2][N:6]2[CH:7]=[CH:8][N:9]=[C:10]([NH:11][CH3:12])[C:5]=12

Participants

4

Reactant 1

HCID 3088360Imidazo(1,2-a)pyrazin-8-amine, 3-bromo-N-methyl-

Product 1

HCID 10351844N-Methylimidazo[1,2-A]pyrazin-8-amineYield 158.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (3-bromo-imidazo[1,2-a]pyrazin-8-yl)-methyl-amine (Example 1) (2.4 g, 11.9 mmol) in methanol (160 ml) was added Pd-C (10% wt. 0.1 eq). The mixture was hydrogenated at rt overnight, filtered, and washed with hot methanol. The organics were combined and concentrated to afford 2.8 g of crude imidazo[1,2-a]pyrazin-8-yl-methyl-amine (M).

Workup

  1. filtrationfiltered
  2. washwashed with hot methanol
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-54ee0e4aaf6b40548e7f26e62a8f6db0
Source dataset
uspto-grants-2007_03
Patent number
US07186832B2

Reaction notes

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