Potassium Carbonate → HCID 73555062, compound

Participants

Reaction Conditions

Reaction Steps

A heavy walled resealable tube was loaded, under an argon atmosphere, with copper (I) oxide (159 mg, 1.11 mmol), 2-(6-bromopyridin-2-yl)-2-methylpropanenitrile (5000 mg, 22.2 mmol), ammonium hydroxide 28% solution (26.9 mL, 444 mmol), K2CO3 (614 mg, 4.44 mmol), N,N-dimethylethylenediamine (196 mg, 244 μA, 2.22 mmol) and ethyleneglycol (44.4 mL). The reaction was heated to 60° C. with stirring for 6 h. After cooling down, the reaction mixture was extracted with dichloromethane (3×25 mL), combined organics dried over magnesium sulfate and evaporated. The residue was purified by flash chromatography (silica gel 50 μm, 40 g, Analogix) eluting with 0 to 5% over 20 min (10% ammonium hydroxide in methanol)/dichloromethane, obtained 2-(6-aminopyridin-2-yl)-2-methylpropanenitrile (3.2 g, 89.4% yield) as a white solid. 1H NMR (CHLOROFORM-d) δ: 7.34-7.46 (m, 1H), 6.81 (d, J=7.2 Hz, 1H), 6.40 (d, J=7.9 Hz, 1H), 4.67 (br. s., 2H), 1.63-1.68 (m, 6H); LC-MS 162.1 [M+H]+.

Provenance & Evidence