Aniline → (3S,6R)-1-[6-Chloro-2-(methylamino)-4-pyrimidinyl]-6-methyl-N-phenyl-3-piperidinecarboxamide

Participants

Reaction Steps

To (3S,6R)-1-[6-chloro-2-(methylamino)-4-pyrimidinyl]-6-methyl-3-piperidinecarboxylic acid (880 mg, 3.09 mmol) in CH2Cl2 (15 mL) at room temperature was added Hunig's base (1.62 mL, 9.27 mmol, 3 equiv) and aniline (0.56 mL, 6.18 mmol, 2 equiv), and the resulting mixture was chilled in an ice bath. To this stirred solution was added HATU (1.29 g, 3.40 mmol, 1.1 equiv) in one portion. The resulting suspension was stirred in the ice bath for 45 minutes. LCMS showed conversion complete. The mixture was filtered, and the filtrate was concentrated in vacuo. Silica gel column chromatography with gradient elution of 1% EtOAc in CHCl3 to 35% EtOAc in CHCl3 gave 700 mg of the title compound. LC-MS (ES) m/z=360 [M+H]+.

Provenance & Evidence