Aluminum(III) Chloride → HCID 178515919, compound

Participants

Reaction Steps

With the exclusion of air and moisture, a mixture of 0.442 g (1.2 mmol) of 4-(3-chloro-phenylamino)-3-(4-methoxy-phenyl)-1H-pyrazolo[3,4-d]pyrimidine [see Example 34], 1.16 g (8.7 mmol) of anhydrous aluminum chloride and 20 ml of benzene is heated under reflux for 45 minutes. The reaction mixture is then poured into ice-water, filtered and washed with water and the filter residue is partitioned between a 5% solution of sodium hydrogen carbonate in water and ethyl acetate. The organic phase is washed with brine, dried over sodium sulfate and concentrated in vacuo. A small amount of hexane is added and the desired product precipitates. Washing with hexane and purification of the crude product by flash chromatography on silica gel (230-400 mesh) using an ethyl acetate/hexane mixture (7:3) yield the title compound; m.p. >220° C.; MS: (M)+ =337.

Provenance & Evidence