Hexane → Ethyl 4-allyl-1-(5-bromopyrimidin-2-yl)piperidine-4-carboxylate

Participants

Reaction Steps

To a solution of ethyl 4-allylpiperidine-4-carboxylate hydrochloride (1.30 g, 6.59 mmol) in EtOH (20.0 mL) was added DIPEA (3.0 mL, 16.47 mmol) and the mixture stirred at rt for 10 min followed by addition of 5-bromo-2-chloropyrimidine (1.06 g, 5.49 mmol). The reaction was then heated up to 70° C. for 1 h. After reaction completion (by TLC), solvent was evaporated and the crude residue purified over 100-200 M silica-gel using 2.0% EtOAc:hexane to obtain the desired product as a yellow solid (1.0 g, 56% yield). 1H NMR (DMSO-d6): δ 1.19 (t, J=6.80 Hz, 3H), 1.44 (m, 2H), 2.02 (m, 2H), 2.27 (m, 2H), 3.10 (m, 2H), 4.13 (q, J=6.80 Hz, 2H), 4.29 (m, 2H), 5.06 (m, 2H), 5.66 (m, 1H) and 8.43 (s, 2H)

Provenance & Evidence