Sodium Carbonate → HCID 18001308, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-bromo-7-methylimidazo[1,2-a]pyrimidine (5.3 g, 25 mmol), 3-methoxyphenylboronic acid (4.94 g, 32.5 mmol) and tetrakis(triphenylphosphine)palladium(0) (870 mg, 0.8 mmol) in 1,2-dimethoxyethane (40 ml) was treated with sodium carbonate (18.8 ml of a 2M aqueous solution) then heated at 85° C. for 16 h. The reaction mixture was allowed to cool to ambient temperature then partitioned between ethyl acetate and water. The organics were washed with 10% sodium carbonate solution, water, brine, dried over anhydrous magnesium sulfate, filtered then pre-adsorbed onto silica. Purification by chromatography on silica gel eluting with dichloromethane:conc. ammonia (99.5:0.5) on a gradient of methanol (1-3%) afforded 3-(3-methoxyphenyl)-7-methylimidazo[1,2-a]pyrimidine as a cream-coloured solid (5.3 g, 89%): δH (400 MHz, CDCl3) 2.66 (3H, s), 3.87 (3H, s), 6.76 (1H, d, J 7), 6.95-6.98 (1H, m), 7.03-7.05 (1H, m), 7.09-7.11 (1H, m), 7.44 (1H, t, J 8), 7.80 (1H, s), 8.52 (1H, d, J 7); m/z (ES+) 240 (M++H).

Provenance & Evidence