Sodium Bicarbonate → 1-(2-(5-Chloro-4-(7-(pyridin-4-yl)benzo[b]thiophen-2-yl)pyrimidin-2-ylamino)ethyl)imidazolidin-2-one

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Reaction Steps

Combine 1-{2-[4-(7-bromo-benzo[b]thiophen-2-yl)-5-chloro-pyrimidin-2-ylamino]-ethyl}-imidazolidin-2-one (81.6 mg, 0.18 mmol), pyridine-4-boronic acid (36.8 mg, 0.3 mmol), and sodium bicarbonate (18.1 mg, 0.2 mmol) in a mixture of water (1 mL) and DMSO (1 mL). Add tetrakis(triphenylphosphine)palladium(0) (10.4 mg, 0.009 mmol). Irradiate the mixture at 150° C. for 15 min with magnetic stirring. Pour the crude reaction mixture onto a strong cation exchange (SCX) (10 g) column. Elute the desired product with 2 N ammonia in methanol (40 mL) and concentrate under reduced pressure. Purify by reverse phase chromatography (30 to 90% gradient at 80 mL/min for 11 min on a 30×100 mm, 5 mm, C18 MS Xterra® column, Solvent A: water with 0.01 M ammonium bicarbonate, Solvent B: acetonitrile) to afford the title compound (20.4 mg, 25.1%). MS (ES) m/z 451 [M+1]+.

Provenance & Evidence