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

HRID 1411934Notes

Reaction equation

HRID 1411934 reaction equation
[CH3:1][N:2]1[CH:7]([CH3:8])[CH2:6][N:5]2[N:9]=[C:10]([N+:12]([O-])=O)[CH:11]=[C:4]2[CH2:3]1.[H][H]>CO.[Ni]>[CH3:1][N:2]1[CH:7]([CH3:8])[CH2:6][N:5]2[N:9]=[C:10]([NH2:12])[CH:11]=[C:4]2[CH2:3]1

Participants

5

Reactant 2

HCID 866844795,6-Dimethyl-2-nitro-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazineHCID 178418361HCID 178418361, compound

Product 1

HCID 866844805,6-Dimethyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-amineYield 86%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of 250d (550 mg, 2.8 mmol) in methanol (20 mL) was added Raney Ni (about 600 mg). The reaction was charged with hydrogen gas (via balloon) and stirred for 2 h at room temperature. It was then filtered through a plug of CELITE® and the filtrate was concentrated under reduced pressure to afford 250e as a yellow solid (400 mg, 86%), which was used directly in the next step without further purification. MS-ESI: [M+H]+ 167.3

Workup

  1. filtrationIt was then filtered through a plug of CELITE®
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-10cdc1b0a6304c6db72326350c06965a
Source dataset
uspto-grants-2014_12
Patent number
US08921353B2

Reaction notes

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