4-nitro-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole → 1-(Tetrahydro-2H-pyran-4-YL)-1H-pyrazol-4-amine

HRID 449883Notes

Reaction equation

HRID 449883 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][N:7]([CH:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH:8]=1)([O-])=O>CO.[Pd]>[O:12]1[CH2:11][CH2:10][CH:9]([N:7]2[CH:8]=[C:4]([NH2:1])[CH:5]=[N:6]2)[CH2:14][CH2:13]1

Participants

4

Reactant 1

HCID 591862964-nitro-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole

Product 1

HCID 510637031-(Tetrahydro-2H-pyran-4-YL)-1H-pyrazol-4-amineYield 78%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To the above 4-nitro-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazole (0.45 g) in MeOH (5 mL) was added 5% Pd/C (0.045 g). The reaction vessel was evacuated and filled with H2 (3×). The reaction was stirred under H2 (1.1 KPa) at room temperature overnight. The mixture was filtered through Celite and concentrated under reduced pressure. The residue was purified by column chromatography (CH2Cl2/MeOH=6/1 then 1/1) to give 1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazol-4-amine (0.17 g, 78% yield for 2 steps). 1H NMR (500 MHz, CDCl3): δ 7.17 (s, 1H), 7.06 (s, 1H), 4.22 (m, 1H), 4.10-4.06 (m, 2H), 3.53-3.49 (m, 2H), 2.06-1.99 (m, 4H). LCMS (ESI) m/z: 168.1 [M+H+].

Workup

  1. customThe reaction vessel was evacuated
  2. additionfilled with H2 (3×)
  3. filtrationThe mixture was filtered through Celite
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography (CH2Cl2/MeOH=6/1

Sources & evidence

ORD record
ord-7d6e59d1ab3745b28483b42525036952
Source dataset
uspto-grants-2013_07
Patent number
US08486950B2

Reaction notes

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