3-(Trifluoromethyl)imidazo[1,5-a]pyrazine → 5,6,7,8-Tetrahydro-3-(trifluoromethyl)imidazo[1,5-a]pyrazine

HRID 1896093Notes

Reaction equation

HRID 1896093 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[N:7]2[CH:8]=[CH:9][N:10]=[CH:11][C:6]2=[CH:5][N:4]=1>C(O)C.[Pd]>[F:13][C:2]([F:1])([F:12])[C:3]1[N:7]2[CH2:8][CH2:9][NH:10][CH2:11][C:6]2=[CH:5][N:4]=1

Participants

4

Reactant 1

HCID 341763213-(Trifluoromethyl)imidazo[1,5-a]pyrazine

Product 1

HCID 341763145,6,7,8-Tetrahydro-3-(trifluoromethyl)imidazo[1,5-a]pyrazineYield 99.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3-Trifluoromethyl-imidazo[1,5-a]pyrazine 1j (12.0 g, 64.2 mmol) was dissolved in 150 mL of anhydrous ethanol, then 10% Pd/C (500 mg) was added to the solution. The reaction mixture was stirred at room temperature under a hydrogen atmosphere for 12 hours. The reaction solution was filtered through a pad of coarse silica gel and the filtrate was concentrated under reduced pressure to obtain the title compound 3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine 1k (12.2 g, yield 99%) as a brown solid. 1H NMR (400 MHz, CDCl3, ppm): δ 6.84 (s, 1H), 4.10 (m, 4H), 3.26 (m, 2H), 1.81 (s, 1H).

Workup

  1. filtrationThe reaction solution was filtered through a pad of coarse silica gel
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e3de90ed91054799bd3515efc3c866ef
Source dataset
uspto-grants-2013_08
Patent number
US08518946B2

Reaction notes

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