Dimethylformamide → HCID 13259452, compound

Participants

Reaction Steps

To a solution of 3.0 g of 1-(m-bromophenyl)-2-oxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidine and 100 ml of dry dimethylformamide was added 0.6 g of 50% sodium hydride and the mixture was stirred for 30 minutes. To this was further added 3.5 g of propargyl bromide and the whole was reacted for one hour at room temperature. After the reaction was complete, the solvent was distilled off from the reaction mixture under reduced pressure. The residue thus obtained was diluted with water to release an oily product, which was then extracted with ether. The ether solution was dehydrated over magnesium sulfate, and separation and purification were accomplished by passing the solution through a column of alumina. The eluate thus obtained was concentrated to give 2.9 g of 1-(m-bromophenyl)-3-propargyl-2-oxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidine as colorless prisms, melting at 118° - 119° C.

Provenance & Evidence