5382-16-1

1722-12-9

893755-98-1

Step 1: Synthesis of 1-(2-pyrimidinyl)-4-piperidinol (180) 4-Hydroxypiperidine (1.5 g, 14.7 mmol), 2-chloropyrimidine (1.5 g, 13.4 mmol) and diisopropylethylamine (6 mL, 33.5 mmol) were dissolved in 50 mL of acetonitrile. The reaction mixture was heated and stirred at 80 °C for 18 hours. After completion of the reaction, the mixture was concentrated to dryness under reduced pressure. The crude product was purified by fast column chromatography using a 0-60% ethyl acetate/hexane gradient elution to afford 2.1 g (81% yield) of target compound 180 as a white solid. 1H NMR (400 MHz, CDCl3): δ 8.28 (d, J = 4.6 Hz, 2H), 6.49 (t, J = 4.8 Hz, 1H), 4.49-4.33 (m, 2H), 4.01-3.88 (m, 1H), 3.37-3.21 (m, 2H), 2.02-1.90 (m, 2H), 1.60- 1.45 (m, 2H); LCMS (ESI): m/z 180 [M + H]+.