5-Isopropyl-2-nitro-4,5-dihydropyrazolo[1,5-a]pyrazin-6(7H)-one → 2-Amino-5-isopropyl-4,5-dihydropyrazolo[1,5-a]pyrazin-6(7H)-one

HRID 407795Notes

Reaction equation

HRID 407795 reaction equation
[CH:1]([N:4]1[C:9](=[O:10])[CH2:8][N:7]2[N:11]=[C:12]([N+:14]([O-])=O)[CH:13]=[C:6]2[CH2:5]1)([CH3:3])[CH3:2].[H][H]>C(O)C.[Pd]>[NH2:14][C:12]1[CH:13]=[C:6]2[CH2:5][N:4]([CH:1]([CH3:2])[CH3:3])[C:9](=[O:10])[CH2:8][N:7]2[N:11]=1

Participants

5

Reactant 2

HCID 866840555-Isopropyl-2-nitro-4,5-dihydropyrazolo[1,5-a]pyrazin-6(7H)-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 866840562-Amino-5-isopropyl-4,5-dihydropyrazolo[1,5-a]pyrazin-6(7H)-oneYield 92.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 151d (220 mg, 1.0 mmol) in ethanol (20 mL) was added Pd/C (10%, 22 mg). The reaction mixture was charged with hydrogen gas (via balloon) and stirred at room temperature for 1 h. The reaction mixture was filtered through a plug of CELITE® and the filtrate was concentrated under reduced pressure to afford 151e as a yellow solid (180 mg, 92%), which was used without further purification. MS-ESI: [M+H]+ 195.3

Workup

  1. filtrationThe reaction mixture was filtered through a plug of CELITE®
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-18b51264df744747acdf7c28e78054de
Source dataset
uspto-grants-2014_06
Patent number
US08754077B2

Reaction notes

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