Imidazo(1,2-a)pyrazine → 5,6,7,8-Tetrahydroimidazo(1,2-a)pyrazine

HRID 1924005Notes

Reaction equation

HRID 1924005 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=12>COCCO.O=[Pt]=O>[N:1]1[CH:2]=[CH:3][N:4]2[CH2:9][CH2:8][NH:7][CH2:6][C:5]=12

Participants

4

Reactant 1

HCID 2771670Imidazo(1,2-a)pyrazine

Product 1

HCID 132470465,6,7,8-Tetrahydroimidazo(1,2-a)pyrazine

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 80192-MethoxyethanolSolvent

Procedure

The imidazo[1,2-a]pyrazine (7.2 g, 60.44 mmole) was dissolved in 2-methoxyethanol (100 ml) and PtO2 (1.2 g, 5.13 mmole) was added. The reaction mixture was stirred overnight at RT in an autoclave under a hydrogen atmosphere (4 bar). The autoclave was then flushed with nitrogen, the reaction mixture was filtered through filter earth, concentrated, and the solvent residues were then extracted with toluene. Purification was carried out by column chromatography on silica gel (DCM/7 N NH3 in methanol, 95:5)

Workup

  1. customThe autoclave was then flushed with nitrogen
  2. filtrationthe reaction mixture was filtered
  3. filtrationthrough filter earth
  4. concentrationconcentrated
  5. extractionthe solvent residues were then extracted with toluene
  6. customPurification

Sources & evidence

ORD record
ord-d2612bf388094df980c972eac51db47e
Source dataset
uspto-grants-2012_05
Patent number
US08178535B2

Reaction notes

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