1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-nitro-1H-pyrazole → 1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1H-pyrazol-3-ylamine

HRID 2381281Notes

Reaction equation

[C:1]([Si:5]([CH3:18])([CH3:17])[O:6][CH2:7][CH2:8][N:9]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[N:10]1)([CH3:4])([CH3:3])[CH3:2].[H][H]>C(OCC)(=O)C.CO.[Pd]>[C:1]([Si:5]([CH3:18])([CH3:17])[O:6][CH2:7][CH2:8][N:9]1[CH:13]=[CH:12][C:11]([NH2:14])=[N:10]1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-3-nitro-1H-pyrazole (500 mg, 1.80 mmol) in ethyl acetate (15 mL) and methanol (15 mL) was treated with 10% palladium on activated carbon (wet, 50 mg) The flask was charged with hydrogen gas via balloon. The reaction stirred at 25° C. for 16 h. The reaction was then filtered through a plug of silica gel (Merck, 60, 40-63 μm) layered with diatomaceous earth and concentrated in vacuo to afford 1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-1H-pyrazol-3-ylamine (391 mg, 90%) as a yellow oil. 1H-NMR (400 MHz, DMSO-d6) δ 0.00 (6H, s), 0.83 (9H, s), 3.78 (2H, t, J=4.8 Hz), 3.87 (2H, t, J=6.0 Hz), 4.48 (2H, s), 5.33 (1H, d, J=2.0 Hz), 7.22 (1H, d, J=2.0 Hz).

Workup

filtrationThe reaction was then filtered through a plug of silica gel (Merck, 60, 40-63 μm)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-c2a967302246429eb7a9dbc737403f60
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08258134B2

Reaction notes

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