1-Butanol → HCID 66920846, compound

Participants

Reaction Conditions

Reaction Steps

A heavy walled, sealable tube suitable for microwave heating was charged with 3 mL of n-butanol and 40 mg (1.7 mmol) of sodium. The mixture was stirred until all of the sodium had reacted, then 212 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 and poured into 10 mL of toluene. The solvents were removed under reduced pressure, then the residue was partitioned between 2 mL of saturated NaHCO3(aq.) solution and 10 mL of toluene. This was concentrated again under reduced pressure, and the residue was taken up in 5 mL of water, then extracted with ethyl acetate (1×10 mL, then 2×5 mL). The combined ethyl acetate layers were back extracted with brine (1×5 mL), dried over MgSO4, filtered, and concentrated to a yellow solid. This was purified via silica gel chromatography, eluting with 50% ethyl acetate/hexanes to provide a white solid. 1H NMR (300 MHz, d6-DMSO) δ 6.19 (s, 2H), 6.14 (s, 2H), 5.31 (s, 1H), 4.18 (t, 2H, J=6.6 Hz), 2.50 (m, 1H), 1.62 (m, 2H), 1.38 (m, 2H), 0.92 (m, 3H, J=7.1 Hz); MS (ESI) m/e=151 (M−Bu+H)+, 207 (M+H)+, 205 (M−H)−.

Provenance & Evidence