Propargyl bromide → HCID 20027319, compound

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Reaction Steps

2-Acetyl-5-aminopyridine, (Journal of Heterocyclic Chemistry, Vol. 10, pp. 1047-1049 (1973)), 25 g (0.161 mol), is dissolved in 600 ml of dry acetone. To this solution is added an 80% solution of propargyl bromide in toluene, 32 ml, and finely powdered potassium carbonate, 27 g. The solution is heated under reflux for thirty-six hours and then allowed to cool to room temperature. The reaction mixture is concentrated in vacuo and the residue is partitioned between dichloromethane and water. The organic portion is separated and the water layer extracted several times with dichloromethane. The combined organics are concentrated in vacuo to a semi-solid residue consisting of a mixture of starting material and a small amount of the monoalkylated product. The residue is triturated with a mixture of toluene and diethyl ether. The solid is removed by filtration and the filtrate is concentrated to an oil. Chromatography of the oil on silica gel with dichloromethane gives the desired product.

Provenance & Evidence