Dimethylamine → HCID 58442389, compound

Participants

Reaction Steps

A mixture of 2-chloro-N-(4-mesitylthiazol-2-yl)isonicotinamide (200 mg, 0.60 mmol, 1.0 equiv), caesium carbonate (2.73 g, 0.6 mmol, 15 equiv) and 2.0 M dimethylamine in THF (3.4 mL, 6.7 mmol, 12 equiv) in DMF (6.0 mL) was heated at reflux for 16 h. The mixture was poured into icy H2O (10.0 mL) and extracted with EtOAc. The organic layer was collected, dried over MgSO4(s), and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (15% EtOAc in hexanes as eluant) to provide 2-(dimethylamino)-N-(4-mesityl-thiazol-2-yl)isonicotinamide (5.5 mg, 0.10 mmol) as yellow solids in 3.0% yield: 1H NMR (CDCl3, 500 MHz) δ 8.32 (d, J=5.1 Hz, 1H), 7.02 (s, 1H), 6.92 (s, 2H), 6.85 (d, J=5.1 Hz, 1H), 6.80 (s, 1H), 3.16 (s, 6H), 2.31 (s, 3H), 2.09 (s, 6H); ESI-MS: m/z 367.1 (M+H)+.

Provenance & Evidence