Methyl 1-(2-chloropyrimidin-4-yl)piperidine-4-carboxylate synthesis

Yield:-

Reaction Conditions:

with triethylamine in methanol at 80; for 24 h;

Steps:

8.A
1.43g Methyl piperidine-4-carboxylate (lOmmol) was mixed with 2.01g 2,4- dichloropyrimidine (13.5mmol) and 3.04g triethylamine in 5OmL methanol. The reaction was heated to 8O⁰C for 24hr. The volatiles were removed in vacuo and the crude residue was purified on silica gel eluted with a linear gradient between 40-60% EtOAc/hexanes. This provided the title compound. ¹H- NMR (CDCl3): δ 1.72-1.82 (m, 2H), 2.00-2.07 (m, 2H), 2.65 (tt, IH, J= 4, 1 IHz), 3.14 (ddd, 2H, J= 3,11 , 14Hz), 3.74 (s, 3H), 4.22 (bs, 2H), 6.42 (d, IH, J= 7Hz), 8.05 (d, IH, J= 7Hz) ppm.

References:

MERCK & CO., INC. WO2006/73589, 2006, A2 Location in patent:Page/Page column 28