Pentanenitrile, 4,4-dimethyl-3-oxo- → 5-Amino-3-tert-butyl-1-(2-methylpyridine-5-yl)pyrazole
反応式
Cl.[NH:2]([C:4]1[CH:5]=[CH:6][C:7]([CH3:10])=[N:8][CH:9]=1)[NH2:3].[CH3:11][C:12]([CH3:19])([CH3:18])[C:13](=O)[CH2:14][C:15]#[N:16]>CCO>[C:12]([C:13]1[CH:14]=[C:15]([NH2:16])[N:2]([C:4]2[CH:9]=[N:8][C:7]([CH3:10])=[CH:6][CH:5]=2)[N:3]=1)([CH3:19])([CH3:18])[CH3:11]参加物
4
実験手順
A mixture of 5-hydrazinyl-2-methylpyridine hydrochloride from Example B27 (5.0 g, 31.4 mmol) and 4,4-dimethyl-3-oxopentanenitrile (8.3 g, 66.3 mmol) in EtOH (50 mL) was heated at reflux overnight. The reaction was concentrated and the residue was dissolved in EtOAc and neutralized with saturated Na2CO3 solution. The organic layer was dried (Na2SO4), concentrated in vacuo and purified by column chromatography to yield 3-tert-butyl-1-(6-methylpyridin-3-yl)-1H-pyrazol-5-amine (5.2 g, 71% yield). 1HNMR (400 MHz, CDCl3) δ 8.72 (s, 1 H), 7.81 (dd, J=8.0, 2.4 Hz, 1 H), 7.23 (d, J=8.4 Hz, 1 H), 5.54 (s, 1 H), 3.71 (br s, 1 H), 2.58 (s, 3 H), 1.29 (s, 9 H); MS (ESI) m/z: 231.2 (M+H+).