N-[4-(bromomethyl)phenyl]acetamide

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a suspension of 35.3 g of 2-(1-piperazinyl)-8-ethyl-5,8-dihydro-5-oxopyrido[2,3-d]pyrimidine-6-carboxylic acid in 500 ml of dimethylformamide was added a solution of 39.0 g of potassium carbonate in 50 ml of water and then 39.5 g of p-acetamidobenzyl bromide. The mixture was heated at 80°-90° C. for 1.5 hours with stirring. After removal of a small amount of the insoluble material by filtration, the filtrate was concentrated to dryness under reduced pressure and the residue was dissolved in 100 ml of water. The solution was adjusted to pH 7.0 with acetic acid. The precipitate was collected by filtration and recrystallized from a mixture of dimethylformamide and ethanol to give the product (42.3 g), m.p. 216.5°-219° C. The mixture was heated at 80°-90° C. for 1.5 hours After removal of a small amount of the insoluble material by filtration the filtrate was concentrated to dryness under reduced pressure the residue was dissolved in 100 ml of water The precipitate was collected by filtration recrystallized from a mixture of dimethylformamide and ethanol