Tri-o-tolylphosphine → 4,6-Diamino-2-propyl-nicotinonitrile

Participants

Reaction Conditions

Reaction Steps

To 5 mg (0.023 mmol) of palladium(II)acetate, 213 mg (1.00 mmol) of 2-bromo-4,6-diaminonicotinonitrile, and 60 mg (0.20 mmol) of tri(o-tolyl)phosphine was added 0.5 mL of DMF. The flask was purged with N2 while stirring, then 5.0 mL of the n-propylzinc iodide solution was via syringe. The mixture was heated at 85° C. for 2.5 hours then cooled. The mixture was poured into a stirred mixture of 20 mL ethyl acetate and 20 mL water, filtered through diatomaceous earth. The filter cake was washed with ethyl acetate (2×5 mL), and the layers were separated. The organic layer was extracted with water (2×20 mL), and brine (1×20 mL), dried over MgSO4, filtered, and concentrated under reduced pressure to an oil. The oil was purified via silica gel chromatography, eluting with 75% ethyl acetate:hexanes to provide 23 mg (13%) of a white solid. 1H NMR (300 MHz, d6-DMSO) δ 6.17 (s, 2H), 6.09 (s, 2H), 5.52 (s, 1H), 2.50 (t, 2H, J=7.6 Hz), 1.62 (m, 2H), 0.90 (t, J=7.3 Hz, 3H); MS (ESI) m/e 177 (M+H)+, 175 (M−H)−.

Provenance & Evidence