5,6-Dimethylpyridin-2-amine

Chemical properties

Light Yellow Low-Melting Solid

Synthesis

A mixture of 2-amino-5-bromo-6-methylpyridine (561 mg, 3.0 mmol), K2CO3 (1.24 g, 9.0 mmol) and Pd(dppf)Cl2·CH2Cl2 (245 mg, 0.30 mmol) was added to a solution of trimethylboroxine (377 mg, 3.0 mmol) in water (1 mL) and dioxane (10 mL). The mixture was heated at reflux for 3 h. After cooling to rt, the mixture was poured into water (50 mL). The mixture was extracted with diethyl ether (3*50ml), and the combined organic phases were dried (Na2SO4) and concentrated. Purification by chromatography (EtOAc/heptane) gave 5,6-Dimethylpyridin-2-amine as a black-brown solid. Yield: 67 %.