Benzyl Bromide → HCID 178481262, compound

Participants

Reaction Steps

To a suspension of 7.1 g. (0.021 mole) of 9-benzyl-2,3-dihydro-1,3-dimethyl-6-(hydroxy)pyrimido[2,1-f]purine-4,8(1H,9H)-dione in 200 ml. of acetone, add 2.3 g. (0.023 mole) of triethylamine, and stir the mixture for 5 minutes at room temperature under a nitrogen atmosphere to obtain a clear solution. Add dropwise to the solution 4.7 g. (0.027 mole) of benzyl bromide, and reflux the mixture for 5 hours under a nitrogen atmosphere. Remove the acetone under reduced pressure, and triturate the gummy residue with methanol. Remove the resultant white solid by filtration, pour the filtrate into water, acidify to pH 4-5 with dilute hydrochloric acid, and decant the aqueous supernatant. Dissolve the gummy residue in the chloroform, wash the solution with water, and dry over anhydrous magnesium sulfate. Remove the drying agent by filtration, and evaporate solvent from the filtrate under reduced pressure. Chromatograph the residual oil on silica gel, eluting with chloroform(96)-methanol(4), to obtain the title compound as a solid with m.p. 176°-179° C.

Provenance & Evidence