Piperazine → HCID 20689199, compound

Participants

Reaction Steps

To an ice cold solution of 1-(S)-(4-hydroxy-pyrimidin-2-yl)-ethyl butyrate (0.42 g, 2.0 mmol) and triethylamine (0.20 g, 2.2 mmol) in methylene chloride (10 mL) was added mesyl chloride (0.25 g, 2.1 mmol) dropwise and stirred for 1.5 h. The mixture was washed successively with saturated bicarbonate and water, and the organic layer dried over anhydrous magnesium sulfate. It was, filtered and evaporated to give 1-(S)-(4-methanesulfonyloxy-pyrimidin-2-yl)-ethyl as an oil. The oil was dissolved in tetahydrofuran (10 mL), and to the solution was added piperazine (0.69 g, 8.0 mmol) and stirred at ambient temperature for 4 hr. The mixture was filtered and the filtrate was concentrated to obtain a crude product which was purified by flash chromatography (9:1 methylene chloride/methanol) to give the title compound as a oil 0.50 g (90%). 1H NMR (CDCl3, 300 MHz) δ0.95 (t, 3H), 1.51 (d, 3H) 1.68 (m, 2), 2.66 (t, 2H), 2.83 (m, 4H), 3.63 (m, 4H), 5.54 (q, 1H), 6.38 (d, 1H), 8.24 (d, 1H); MS (Cl) 251 (MH+).

Provenance & Evidence