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 1919087Notes

Reaction equation

HRID 1919087 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]>[Pd].C(O)C>[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

4

Reactant 1

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

Product 1

HCID 580439485-Ethyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-amineYield 71%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A 500-mL Parr hydrogenation bottle was charged with 285a (1.8 g, 9 mmol), 10% palladium on carbon (50% wet, 500 mg dry weight) and ethanol (100 mL). The bottle was evacuated, charged with hydrogen gas to a pressure of 50 psi and shaken for 1 h on a Parr hydrogenation apparatus. The catalyst was removed by filtration through a pad of Celite 521 washing with 1:1 methylene chloride:methanol (500 mL). The resulting solution was concentrated under reduced pressure to afford a 71% yield (1.7 g) of crude 285b.

Workup

  1. customThe bottle was evacuated
  2. additioncharged with hydrogen gas to a pressure of 50 psi
  3. customThe catalyst was removed by filtration through a pad of Celite 521 washing with 1:1 methylene chloride
  4. concentrationThe resulting solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-093044cbec484052acd59326966dbd85
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

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