5-Ethyl-2-nitro-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine → 5-Ethyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-amine

HRID 337309Notes

Reaction equation

HRID 337309 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]2[N:9]=[C:10]([N+:12]([O-])=O)[CH:11]=[C:5]2[CH2:4]1)[CH3:2]>[Pd].CCO>[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]2[N:9]=[C:10]([NH2:12])[CH:11]=[C:5]2[CH2:4]1)[CH3:2]

Participants

4

Reactant 1

HCID 580439255-Ethyl-2-nitro-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine

Product 1

HCID 580439485-Ethyl-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazin-2-amineYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

In a 250 mL round-bottomed flask, 5-ethyl-2-nitro-4,5,6,7-tetrahydro -pyrazolo[1,5-a]pyrazine (427 mg, 2.17 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 (115 mg, 1.08 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 (350 mg). (M+H)+=167 m/e. 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 1.16 (t, J=7.18 Hz, 3 H) 2.59 (q, J=7.18 Hz, 2 H) 2.79-3.03 (m, 2 H) 3.57 (overlapping s, 4 H) 3.87-4.12 (m, 2 H) 5.35 (s, 1 H).

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-419404430aaa40b6b9aeb1a97f1b2c1c
Source dataset
uspto-grants-2014_11
Patent number
US08889682B2

Reaction notes

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