1-(2-methyl-2-triethylsilanyloxy-propyl)-3-nitro-1H-pyrazole → 1-(2-methyl-2-triethylsilanyloxy-propyl)-1H-pyrazol-3-ylamine

HRID 546126Notes

Reaction equation

HRID 546126 reaction equation
[CH3:1][C:2]([O:13][Si:14]([CH2:19][CH3:20])([CH2:17][CH3:18])[CH2:15][CH3:16])([CH3:12])[CH2:3][N:4]1[CH:8]=[CH:7][C:6]([N+:9]([O-])=O)=[N:5]1.[H][H]>[Pd].C(O)C>[CH3:1][C:2]([O:13][Si:14]([CH2:17][CH3:18])([CH2:15][CH3:16])[CH2:19][CH3:20])([CH3:12])[CH2:3][N:4]1[CH:8]=[CH:7][C:6]([NH2:9])=[N:5]1

Participants

5

Reactant 2

HCID 584370871-(2-methyl-2-triethylsilanyloxy-propyl)-3-nitro-1H-pyrazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 584371291-(2-methyl-2-triethylsilanyloxy-propyl)-1H-pyrazol-3-ylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

In a Parr shaker bottle was placed 1-(2-methyl-2-triethylsilanyloxy-propyl)-3-nitro-1H-pyrazole (197 mg, 0.65 mmol), 10% palladium on activated carbon (25 mg) and ethanol (10 mL). The bottle was then placed on the Parr shaker at 50 psi of hydrogen pressure for 1 h. The reaction was then filtered through a pad of celite and washed with ethanol, concentration in vacuo afforded 1-(2-methyl-2-triethylsilanyloxy-propyl)-1H-pyrazol-3-ylamine (191 mg, 100% (wet with some ethanol)) as a clear colorless oil: ES-HRMS m/e calcd for C13H27N3OSi (M+H)+ 270.1996, observed 270.1995; 1H NMR (300 MHz, CDCl3) δ ppm 0.56 (q, J=7.9 Hz, 6H, 3×SiCH2), 0.92 (t, J=7.9 Hz, 9H, 3×CH3), 1.21 (s, 6H, 2×CH3), 2.63 (br.s., 2H, NH2), 3.83 (s, 2H, NCH2), 5.59 (d, J=2.4 Hz, 1H, Ar), 7.22 (d, J=2.4 Hz, 1H, Ar).

Workup

  1. filtrationThe reaction was then filtered through a pad of celite
  2. washwashed with ethanol, concentration in vacuo

Sources & evidence

ORD record
ord-0e858687c94f4775ac58e34fecceea37
Source dataset
uspto-grants-2011_05
Patent number
US07935699B2

Reaction notes

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