Pentanenitrile, 4,4-dimethyl-3-oxo- → 5-Amino-3-tert-butyl-1-(2-methylpyridine-5-yl)pyrazole

HRID 871699Notes

Reaction equation

[CH3:1][C:2]([CH3:9])([CH3:8])[C:3](=O)[CH2:4][C:5]#[N:6].[NH:10]([C:12]1[CH:13]=[CH:14][C:15]([CH3:18])=[N:16][CH:17]=1)[NH2:11]>CCO>[C:2]([C:3]1[CH:4]=[C:5]([NH2:6])[N:10]([C:12]2[CH:17]=[N:16][C:15]([CH3:18])=[CH:14][CH:13]=2)[N:11]=1)([CH3:9])([CH3:8])[CH3:1]

Participants

Conditions

Temperature: 80 °C

Procedure

Using the procedure described in Example 308A Step 1, to a solution of 4,4-dimethyl-3-oxopentanenitrile (782 mg, 6.25 mmol) in anhydrous EtOH (30 ml) was added 5-hydrazinyl-2-methylpyridine (1 g, 8.12 mmol) and the reaction mixture was heated at 80° C. overnight. The residue was purified by silica gel chromatography (DCM/EtOAc 10-50%) to afford 3-tert-butyl-1-(6-methylpyridin-3-yl)-1H-pyrazol-5-amine (95 mg, 7%). 1H NMR (300 MHz, CDCl3) δ 1.34 (s, 9H), 2.59 (s, 3H), 3.67 (brs, 2H), 5.56 (s, 1H), 7.25 (d, J=9 Hz, 1H), 7.81 (d, J=9 Hz, 1H), 8.74 (s, 1H); LC-MS (ESI) m/z 231 (M+H)+.

Workup

customThe residue was purified by silica gel chromatography (DCM/EtOAc 10-50%)

Sources & evidence

ORD record: ord-bf39454a8ce843cf83ff30370955d562
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08969587B2

Reaction notes

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