Iodoethane → Ethyl 1-(5-bromopyrimidin-2-yl)-4-ethoxypiperidine-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

To an ice-cold solution of ethyl 1-(5-bromopyrimidin-2-yl)-4-hydroxypiperidine-4-carboxylate (0.50 g, 1.51 mmol) in DMF (5 mL) was added NaH (0.066 g, 1.67 mmol, 60% dispersion in mineral oil) portion wiseand the mixture stirred at 0° C. for 10 minutes followed by drop wise addition of ethyl iodide (0.58 mL, 7.57 mmol). The reaction was stirred at 0° C. for 2 h. After completion of reaction (by TLC), the reaction was quenched with saturated NH4Cl solution (100 mL), extracted with EtOAc (3×100 mL) and the combined organics washed with water and brine and dried over Na2SO4. The crude residue was purified over 100-200 M silica-gel using 10% EtOAc:hexane to obtain the desired product as a yellow liquid (0.24 g, 44% yield). 1H NMR (DMSO-d6): δ 8.27 (s, 2H), 4.31 (m, 2H), 4.22 (q, J=6.40 Hz, 2H), 3.44 (m, 4H), 1.96 (m, 4H), and 1.28 (m, 6H).

Provenance & Evidence