5-Ethyl-2-nitro-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine → 5-Ethyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-amine

HRID 1021945Notes

Reaction equation

HRID 1021945 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]2[N:9]=[C:10]([N+:12]([O-])=O)[CH:11]=[C:5]2[CH2:4]1)[CH3:2].[H][H]>[Pd].CO>[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]2[N:9]=[C:10]([NH2:12])[CH:11]=[C:5]2[CH2:4]1)[CH3:2]

Participants

5

Reactant 2

HCID 580439255-Ethyl-2-nitro-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazineHCID 178418361HCID 178418361, compound

Product 1

HCID 580439485-Ethyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-amineYield 84.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A 50-mL single-neck round-bottomed flask was purged with nitrogen and charged with 208a (1.4 g, 7.1 mmol), 10% palladium on carbon (50% wet, 208 mg), methanol (30 mL), and hydrogen gas. The mixture was stirred at room temperature under hydrogen atmosphere for 2 h. The catalyst was removed by filtration through a pad of CELITE® and the filtrate was concentrated under reduced pressure to afford 208b (1.0 g, 84%) as yellow oil. MS-ESI: [M+H]+ 167

Workup

  1. customA 50-mL single-neck round-bottomed flask was purged with nitrogen
  2. customThe catalyst was removed by filtration through a pad of CELITE®
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d813d6f76b264e80994b50df7e12d4a6
Source dataset
uspto-grants-2014_05
Patent number
US08716274B2

Reaction notes

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