Sodium Carbonate → HCID 60204320, compound

Participants

Reaction Conditions

Reaction Steps

A 5 mL Personal Chemistry microwave tube was charged with 1-(2-(4-(benzo[b]thiophen-2-yl)-5-bromopyrimidin-2-ylamino)ethyl)-5,5-dimethylimidazolidine-2,4-dione (103 mg, 0.22 mmol), phenyl boronic acid (55 mg, 0.44 mmol), a 2 M aqueous solution of sodium carbonate (0.22 mL, 0.44 mmol), dioxane (2 mL) and tetrakis(triphenylphosphine)palladium (0) (52 mg, 0.044 mmol). The vessel was sealed and heated to 140° C. for 20 min with stirring. After cooling to r.t. the mixture was diluted with ethyl acetate (10 mL) and washed with a saturated aqueous solution of sodium hydrogen carbonate (10 mL). The organic layer was separated, dried over magnesium sulfate, filtered and the solvent evaporated in vacuo. The residue was purified by flash chromatography (chloroform/methanol 99:1 to 96:4 followed by a second column: ethyl acetate/hexane/methanol 50:48:2) to afford the title compound (17 mg, 17%). 1H NMR: δ (CDCl3, 400 MHz) 1.47 (s, 6 H), 3.60-3.68 (m, 2 H), 3.81-3.92 (m, 2 H), 6.32 (br. s., 1 H), 6.92 (s, 1 H), 7.26 (t, J=7 Hz, 1 H), 7.32 (t, J=7 Hz, 1 H), 7.36 (dd, J=3 Hz, 2 H), 7.44-7.47 (m, 3 H), 7.50 (d, J=8 Hz, 1 H), 7.79 (d, J=8 Hz, 1 H), 8.22 (s, 1 H): HRMS (M+H)+ Calcd. C25H23N5O2S 458.1650, found 458.1616

Provenance & Evidence