HCID 58044079, compound → HCID 134153925, compound

Participants

Reaction Conditions

Reaction Steps

TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (44.2 mg, 0.05 mmol) was added to 5-(2-(dimethylamino)ethoxy)pyridin-2-amine (175 mg, 0.97 mmol), 1-(6-chloro-5-methylpyrimidin-4-yl)-1H-benzo[d]imidazole (236 mg, 0.97 mmol), sodium t-butoxide (139 mg, 1.45 mmol) and (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (84 mg, 0.14 mmol) in toluene (10 mL) at 20°C under nitrogen. The resulting suspension was stirred at 100 °C for 16 hours then cooled to room temperature. LCMS analysis indicates no SM, product peak present. The reaction mixture was diluted with DCM/MeOH, filtered and filtrate concentrated _in vacuo_. The residue was dissolved in DCM (100 mL) and washed with water (100 mL). The organic layer was passed through phase separating cartridge and concentrated under reduced pressure. The crude product was purified by preparative HPLC (Waters XBridge Prep C18 OBD column, 5µ silica, 19 mm diameter, 100 mm length), using decreasingly polar mixtures of water (containing 1% NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford 6-(1H-benzo[d]imidazol-1-yl)-N-(5-(2-(dimethylamino)ethoxy)pyridin-2-yl)-5-methylpyrimidin-4-amine (67.0 mg, 17.82 %) as a yellow solid.

Provenance & Evidence