5-(1-Methoxypropan-2-yl)-2-nitro-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine → 5-(1-Methoxypropan-2-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-amine

HRID 593093Notes

Reaction equation

HRID 593093 reaction equation
[CH3:1][O:2][CH2:3][CH:4]([N:6]1[CH2:11][CH2:10][N:9]2[N:12]=[C:13]([N+:15]([O-])=O)[CH:14]=[C:8]2[CH2:7]1)[CH3:5].[H][H]>CCO.[Pd]>[CH3:1][O:2][CH2:3][CH:4]([N:6]1[CH2:11][CH2:10][N:9]2[N:12]=[C:13]([NH2:15])[CH:14]=[C:8]2[CH2:7]1)[CH3:5]

Participants

5

Reactant 2

HCID 866845445-(1-Methoxypropan-2-yl)-2-nitro-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazineHCID 178418361HCID 178418361, compound

Product 1

HCID 866845455-(1-Methoxypropan-2-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-amineYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 300a (600 mg, 2.5 mmol) in EtOH (40 mL) was added Pd/C (10%, 60 mg). The reaction mixture was charged with hydrogen gas (via balloon) and stirred at room temperature for 2 h. After reaction was complete, the mixture was filtered through a plug of CELITE®. The filtrate was concentrated reduced pressure to afford 300b as a yellow solid (467 mg, 89%), which was used without further purification. MS-ESI: [M+H]+ 211.1

Workup

  1. customAfter reaction
  2. filtrationthe mixture was filtered through a plug of CELITE®
  3. concentrationThe filtrate was concentrated reduced pressure

Sources & evidence

ORD record
ord-e4f1e1bc4ac049b3a601e45f9a10ceca
Source dataset
uspto-grants-2016_01
Patent number
US09238655B2

Reaction notes

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