1-(Pyrimidin-2-yl)ethan-1-one → 2-(Pyrimidin-2-yl)but-3-yn-2-ol

A solution of 1-(pyrimidin-2-yl)ethan-1-one (2.5 g, 20.47 mmol) in tetrahydrofuran (60 mL) was added dropwise into a ethynylmagnesium bromide (0.5 M in tetrahydrofuran, 60 mL, 30 mmol) solution with stirring at room temperature under nitrogen atmosphere. The reaction mixture was stirred at room temperature for 1 hr and then quenched by the addition of saturated aqueous ammonium chloride (200 mL). The resulting solution was extracted with ethyl acetate (2×300 mL) and the combined organic layers were washed with brine (300 mL), dried over anhydrous sodium sulphate and concentrated in vacuo. The residue was purified on a silica gel column, elution with ethyl acetate/petroleum ether (0:1-1:1) afforded 2-(pyrimidin-2-yl)but-3-yn-2-ol (1.5 g, 50%) as yellow oil. 1H NMR (400 MHz, CDCl3) delta 8.82 (d, J=4.4 Hz, 2H), 7.33-7.29 (m, 1H), 5.1 (s, 1H), 2.56 (s, 1H), 1.93 (s, 3H); LC-MS: m/z=149 (M+H)+.

1. stirringThe reaction mixture was stirred at room temperature for 1 hr
2. customquenched by the addition of saturated aqueous ammonium chloride (200 mL)
3. extractionThe resulting solution was extracted with ethyl acetate (2×300 mL)
4. washthe combined organic layers were washed with brine (300 mL)
5. dry with materialdried over anhydrous sodium sulphate
6. concentrationconcentrated in vacuo
7. customThe residue was purified on a silica gel column, elution with ethyl acetate/petroleum ether (0:1-1:1)

ORD 기록

ord-9f0572dcaa0c4426954a535badda2df3

출처 데이터셋

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08901313B2