Ethyl Acetate → HCID 58504673, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 2,4,6-trichloropyrimidine (0.18 mL, 1.59 mmol) and N-cyclohexyl-6-(trifluoromethyl)-3-piperidinecarboxamide (0.5 g, 1.588 mmol) in 1,4-dioxane (15 mL) was added Hunig's base (0.56 mL, 3.18 mmol), and the reaction mixture was stirred over the weekend (3 days) at 80° C. into a sealed tube. Approximately 35% starting material was remaining. The temperature was increased to 140° C., and the reaction mixture was stirred at this temperature for 3 hours. The reaction was then heated for 1 hour at 160° C. Since there was still remaining starting material, the reaction was stirred overnight at 140° C. The reaction mixture was poured onto water and EtOAc. The organic layer was separated, washed with brine, dried (MgSO4), filtered and concentrated. Flash chromatography on SiO2 (gradient: 100% Hexanes to 50% EtOAc in Hexanes) afforded the title compound (239 mg) as a white solid, and the corresponding regioisomer (196 mg) as a white solid. LC-MS (ES) m/z=425, 427 [M+H]+.

Provenance & Evidence