Ethylene Glycol → 4,6-Diamino-2-(2-hydroxy-ethoxy)-nicotinonitrile

Participants

Reaction Conditions

Reaction Steps

A heavy walled, sealable tube suitable for microwave heating was charged with 3 mL of ethylene glycol and 50 mg (2.2 mmol) of sodium. The mixture was stirred at 95° C. until all of the sodium had reacted, then 213 mg (1.00 mmol) of 2-bromo-4,6-diaminonicotinonitrile was added. The tube was sealed, and the mixture was heated with a microwave apparatus at 150° C. for 10 minutes then cooled. The mixture was diluted with 15 mL of water, and extracted with ethyl acetate (3×5 mL). The combined ethyl acetate layers were back extracted with water (1×5 mL), and brine (1×5 mL), dried over MgSO4, filtered, and concentrated to provide 85 mg (44%) of a solid. 1H NMR (300 MHz, d6-DMSO) δ 6.20 (s, 2H), 6.16 (s, 2H), 5.32 (s, 1H), 4.76 (t, 1H, J=5.3 Hz), 4.21 (m, 2H), 3.64 (q, 2H, J=5.4 Hz); MS (ESI) m/e=151 (M−EtOH+H)+, 195 (M+H)+.

Provenance & Evidence