Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[C:7](=[O:9])[CH3:8].[C:10]([Mg]Br)#[CH:11]>O1CCCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[C:7]([OH:9])([C:10]#[CH:11])[CH3:8]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
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)+.
Workup
- stirringThe reaction mixture was stirred at room temperature for 1 hr
- customquenched by the addition of saturated aqueous ammonium chloride (200 mL)
- extractionThe resulting solution was extracted with ethyl acetate (2×300 mL)
- washthe combined organic layers were washed with brine (300 mL)
- dry with materialdried over anhydrous sodium sulphate
- concentrationconcentrated in vacuo
- customThe residue was purified on a silica gel column, elution with ethyl acetate/petroleum ether (0:1-1:1)
Sources & evidence
- ORD record
- ord-9f0572dcaa0c4426954a535badda2df3
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08901313B2
Linked notes
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