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

HRID 1013741Notes

Reaction equation

HRID 1013741 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=12>[Pd].Cl.CCO>[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 23938PalladiumCatalystHCID 21887872Ethanol hydrochlorideSolvent

Procedure

Imidazo[1,2-a]pyrazine (250 mg, 2.1 mmol) and palladium on carbon (10%) (55.8 mg, 0.53 mmol) were placed in a pressure resistant bottle and suspended under nitrogen in 0.5M HCl/EtOH. The mixture was stirred under at 45 psi H2 for 16 hrs. LC/MS showed completion. The next day, the reaction mixture was passed through celite cake. The filtrate was concentrated under reduced pressure to afford a tan solid. This was used directly without further purification. MS: [N+H]=124.2; Calc'd for C6H9N3: 123.2.

Workup

  1. concentrationThe filtrate was concentrated under reduced pressure
  2. customto afford a tan solid
  3. customThis was used directly without further purification

Sources & evidence

ORD record
ord-6e4a85c1c31443be9c2b526c2ad8fc23
Source dataset
uspto-grants-2011_07
Patent number
US07981891B2

Reaction notes

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