2,5-Hexanedione → HCID 68941558, compound

Participants

Reaction Steps

A mixture of 3-[6-(4-bromo-phenyl)-5-(4-chloro-phenyl)-4-oxo-4,5-dihydro-pyrazolo[3,4-d]pyrimidin-1-yl]-benzene sulfonamide (prepared as described in example 6, 10.00 g, 17.95 mmol), hexane-2,5-dione (6.14 g, 53.9 mmol), and p-toluenesulfonic acid monohydrate (1.000 g, 5.257 mmol) in dry toluene (250 mL) is heated to reflux in a Dean-Stark apparatus for 18 h. The reaction mixture is concentrated and the residue obtained is stirred in ethyl acetate and filtered. About 7.1 g of starting material is recovered. Concentration of the filtrate afforded the crude product. It is then purified by column chromatography (silica gel, 60-120 mesh) to afford the 6-(4-bromo-phenyl)-5-(4-chloro-phenyl)-1-[3-(2,5-dimethyl-pyrrole-1-sulfonyl)-phenyl]-1,5-dihydro-pyrazolo[3,4-d]pyrimidin-4-one.

Provenance & Evidence