Réaction #792213

Équation de réaction

sodium chloride

2-(6-bromopyridin-2-yl)pyrimidine

N-isopropylpropane-2-amine

ethynyl(trimethyl)silane

→

2-{6-[(Trimethylsilyl)ethynyl]pyridin-2-yl}pyrimidine

Solvants

tetrahydrofuran

Conditions de réaction

Traitement

1. 1
   Autredegassed in an ultrasonic bath under argon
2. 2
   Filtrationthe mixture was filtered through Celite
3. 3
   Extractionthe aqueous phase was extracted repeatedly with ethyl acetate
4. 4
   SéchageThe combined organic phases were dried over magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated
7. 7
   Autrepurified chromatographically

Mode opératoire

1.00 g (3.99 mmol) of 2-(6-bromopyridin-2-yl)pyrimidine, 45.5 mg (239 μmol) of copper(I) iodide and 670 μl (4.78 mmol) of N-isopropylpropane-2-amine were initially charged in 15 ml of tetrahydrofuran and degassed in an ultrasonic bath under argon. The reaction mixture was then heated to 50° C., 168 mg (239 mol) of dichloro[bis(triphenylphosphoranyl)]palladium were added and 1.70 ml (12.0 mmol) of ethynyl(trimethyl)silane were added dropwise over a period of one hour. The mixture was then stirred at 60° C. for a further two hours. For work-up, the mixture was added to semiconcentrated sodium chloride solution, the mixture was filtered through Celite and the aqueous phase was extracted repeatedly with ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered, concentrated and purified chromatographically. This gave 520 mg (51% of theory) of 2-{6-[(trimethylsilyl)ethynyl]pyridin-2-yl}pyrimidine.

Source