2-Nitro-5-(oxetan-3-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine → 5-(Oxetan-3-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-amine

HRID 337306Notes

Reaction equation

HRID 337306 reaction equation
[N+:1]([C:4]1[CH:16]=[C:7]2[CH2:8][N:9]([CH:12]3[CH2:15][O:14][CH2:13]3)[CH2:10][CH2:11][N:6]2[N:5]=1)([O-])=O>[Pd].CCO>[O:14]1[CH2:15][CH:12]([N:9]2[CH2:10][CH2:11][N:6]3[N:5]=[C:4]([NH2:1])[CH:16]=[C:7]3[CH2:8]2)[CH2:13]1

Participants

4

Reactant 1

HCID 667429562-Nitro-5-(oxetan-3-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine

Product 1

HCID 667430935-(Oxetan-3-yl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-amineYield 95.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

In a 250 mL round-bottomed flask, 2-nitro-5-oxetan-3-yl-4,5,6,7-tetrahydro-pyrazolo[1,5-a]pyrazine (674 mg, 2.99 mmol, Eq: 1.00) was combined with EtOH (50 ml) to give a light yellow suspension. The reaction mixture was vacuum flushed three times with argon then 10% Pd/C (159 mg, 1.5 mmol, Eq: 0.5) was added and the reaction mixture was stirred under hydrogen balloon overnight. The reaction was filtered through a pad of celite. The celite pad was washed with ethanol. The combined filtrate and washes were concentrated in vacuo to afford the desired product (555 mg). (M+H)+=195 m/e.

Workup

  1. customto give a light yellow suspension
  2. customflushed three times with argon
  3. filtrationThe reaction was filtered through a pad of celite
  4. washThe celite pad was washed with ethanol
  5. concentrationThe combined filtrate and washes were concentrated in vacuo

Sources & evidence

ORD record
ord-250f178d48814faab3db0535efc08cb6
Source dataset
uspto-grants-2014_11
Patent number
US08889682B2

Reaction notes

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