4,6-Dichloro-2-(methylthio)pyrimidine → HCID 86659191, compound

Participants

Reaction Steps

To cis-6-(trifluoromethyl)-3-piperidinecarboxylic acid (3.393 g, 14.52 mmol) in THF (1.5 mL) were added molecular sieves, and the resulting mixture was stirred for 5 minutes into a 250 mL RB flask. The mixture was cooled in an ice bath, and then LiHMDS (43.6 mL, 43.6 mmol) was added slowly. After the addition was completed, 4,6-dichloro-2-(methylthio)pyrimidine (3.40 g, 17.43 mmol) was added. After 0.5 hours, the reaction was quenched with 30 mL of water and by the dropwise addition of 6N HCl until pH was acidic. The resulting mixture was extracted with EtOAc (3×30 mL). The organics were combined, washed with brine, dried (MgSO4), filtered and concentrated to afford the crude title compound as an oil. LC-MS (ES) m/z=356 [M+H]+.

Provenance & Evidence