2-Methyl-1-(2-nitro-6,7-dihydropyrazolo[1,5-a]pyrazin-5(4H)-yl)propan-1-one → 1-(2-Amino-6,7-dihydropyrazolo[1,5-a]pyrazin-5(4H)-yl)-2-methylpropan-1-one

HRID 407775Notes

Reaction equation

HRID 407775 reaction equation
[CH3:1][CH:2]([CH3:17])[C:3]([N:5]1[CH2:10][CH2:9][N:8]2[N:11]=[C:12]([N+:14]([O-])=O)[CH:13]=[C:7]2[CH2:6]1)=[O:4]>CO.[Pd]>[NH2:14][C:12]1[CH:13]=[C:7]2[CH2:6][N:5]([C:3](=[O:4])[CH:2]([CH3:1])[CH3:17])[CH2:10][CH2:9][N:8]2[N:11]=1

Participants

4

Reactant 1

HCID 866840382-Methyl-1-(2-nitro-6,7-dihydropyrazolo[1,5-a]pyrazin-5(4H)-yl)propan-1-one

Product 1

HCID 866840391-(2-Amino-6,7-dihydropyrazolo[1,5-a]pyrazin-5(4H)-yl)-2-methylpropan-1-oneYield 98.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 148a (220 mg, 0.924 mmol) in methanol (20 mL) was added Pd/C (22 mg). The system was evacuated and refilled with H2. After stirring at room temperature for 2 h, the mixture was filtered. The filtrate was concentrated under reduced pressure to afford 148b as a yellow solid (190 mg, 98%), which was used in the next step without further purification. MS-ESI: [M+H]+ 209.1

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-45bd10701825416e805c8d5d437e78c4
Source dataset
uspto-grants-2014_06
Patent number
US08754077B2

Reaction notes

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