Sodium Iodide → HCID 15547169, compound

Participants

Reaction Steps

160 mg of potassium carbonate and 50 mg of sodium iodide are added to 300 mg of 4-[(3-chloro-4-fluorophenyl)amino]-6-cyclopentyloxy-7-[2-(piperazin-1-yl)-ethoxy]-quinazoline in 20 ml of acetonitrile. Then 170 mg of (R)-5-[(methanesulphonyl-oxy)methyl]-2-oxo-tetrahydrofuran are added. The reaction mixture is refluxed for four hours, then a further 0.10 g of (R)-5-[(methanesulphonyloxy)methyl]-2-oxo-tetrahydrofuran are added. After another ten hours of refluxing a further 0.12 g of (R)-5-[(methanesulphonyloxy)methyl]-2-oxo-tetrahydrofuran as well as 0.20 g of potassium carbonate and 70 mg of sodium iodide are added. The reaction mixture is refluxed for another five hours and then left to stand over a weekend. For working up the reaction mixture is filtered and the filtrate is concentrated by evaporation. The crude product is purified by chromatography over a silica gel column with methylene chloride/methanol/concentrated aqueous ammonia solution (95:5:0.05, later 93:7:0.1) as eluant. The title compound is obtained as a white solid.

Provenance & Evidence