Water → 1-(5-Propylpyrimidin-2-yl)piperidin-4-ol

Participants

Reaction Steps

A solution of piperidin-4-ol (5.549 g, 54.9 mmol), 2-chloro-5-propylpyrimidine (8.59 g, 54.9 mmol) and K2CO3 (22.75 g, 165 mmol) in DMF (54.9 mL) was heated to 90° C., where it stirred for 15 hrs. After this time, the reaction mixture was cooled to rt. Once at the prescribe temperature, H2O (80 mL) was added and the resulting mixture was extracted with EtOAc (3×16 mL). The combined organic layers were dried (MgSO4), filtered and then concentrated to yield a residue. The residue was purified by column chromatography (silica gel, hexanes-EtOAc gradient 0 to 100% EtOAc) to afford 1-(5-propylpyrimidin-2-yl)piperidin-4-ol as a white solid (11.9 g, 97% yield). 1H NMR (400 MHz, chloroform-d) δ ppm 8.15 (s, 2H), 4.40 (dt, J=13.7, 4.4 Hz, 2H), 3.95 (td, J=8.9, 4.7 Hz, 1H), 3.27 (ddd, J=13.3, 10.0, 3.0 Hz, 2H), 2.40 (t, J=7.7 Hz, 2H), 1.87-2.05 (m, 2H), 1.44-1.65 (m, 5H), 0.94 (t, J=7.4 Hz, 3H).

Provenance & Evidence