1-(2-Nitro-6,7-dihydropyrazolo[1,5-a]pyrazin-5(4H)-yl)propan-1-one → 1-{2-amino-4H,5H,6H,7H-pyrazolo[1,5-a]pyrazin-5-yl}propan-1-one

HRID 593024Notes

Reaction equation

HRID 593024 reaction equation
[N+:1]([C:4]1[CH:16]=[C:7]2[CH2:8][N:9]([C:12](=[O:15])[CH2:13][CH3:14])[CH2:10][CH2:11][N:6]2[N:5]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:16]=[C:7]2[CH2:8][N:9]([C:12](=[O:15])[CH2:13][CH3:14])[CH2:10][CH2:11][N:6]2[N:5]=1

Participants

4

Reactant 1

HCID 866845021-(2-Nitro-6,7-dihydropyrazolo[1,5-a]pyrazin-5(4H)-yl)propan-1-one

Product 1

HCID 866845031-{2-amino-4H,5H,6H,7H-pyrazolo[1,5-a]pyrazin-5-yl}propan-1-oneYield 99.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 265a (260 mg, 1.16 mmol) in methanol (10 mL) was added 10% Pd/C (26 mg). The system was evacuated and then refilled with H2. After stirring for 2 h, analysis of the reaction mixture by LCMS showed complete conversion to the desired product. The mixture was filtered, and the filtrate was concentrated under reduced pressure to afford 265b as a yellow solid (225 mg, 99%). MS-ESI: [M+H]+ 195.1

Workup

  1. customThe system was evacuated
  2. additionrefilled with H2
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-9c44cf55d28e416d802f296716bd7bbd
Source dataset
uspto-grants-2016_01
Patent number
US09238655B2

Reaction notes

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