4,6-Dichloropyrimidine → HCID 86659170, compound

Participants

Reaction Steps

To cis-N-cyclohexyl-6-(trifluoromethyl)-3-piperidinecarboxamide (1.0 g, 3.2 mmol) in THF (15 mL) was added 1M LiHMDS in THF (11 mL, 11.00 mmol) at room temperature. After 5 minutes, 4,6-dichloro-2-(methylthio)pyrimidine (0.620 g, 3.18 mmol) was added. After 10 minutes, LCMS analysis of the reaction mixture indicated the presense of ˜85% desired product+13% of dichloropyrimidine SM. The reaction mixture was poured onto saturated NH4Cl and EtOAc. The organic layer was separated, washed with brine, dried (MgSO4), filtered and concentrated. A solid cartridge was prepared by adding EtOAc (˜200 mL) to the crude and SiO2 (3 g). The mixture was concentrated. Flash chromatography (100% Hexanes to 50% EtOAc in Hexanes, then 100% EtOAc) afforded the title compound (690 mg) as an off-white solid. LC-MS (ES) m/z=437, 439 [M+H]+.

Provenance & Evidence