Potassium Carbonate → HCID 57785847, compound

Participants

Reaction Conditions

Reaction Steps

Methanesulfonyl chloride (1.10 mL, 13.4 mmol) was added to a stirred solution of methyl 4-chloro-2-[(4,6-diethyl-2-methylpyrimidin-5-yl)amino]-1-(3-hydroxypropyl)-1H-benzimidazole-7-carboxylate (Reference example 125, 2.90 g, 6.71 mmol) and triethylamine (2.8 mL) in tetrahydrofuran (35 mL) at 0° C. The mixture was stirred at 0° C. for 90 min, and concentrated in vacuo. A mixture of the resulting mesylate and potassium carbonate (2.78 g, 20.1 mmol) in N,N-dimethylformamide (30 mL) was stirred at 70° C. for 4 hr. The mixture was diluted with water, and extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a 70-100% ethyl acetate/n-hexane gradient mixture. The filtrate was concentrated in vacuo to give the title compound as a colorless solid (2.21 g, 5.34 mmol, 80% in 2 steps).

Provenance & Evidence