Aluminum(III) Chloride → CGP-59326

Participants

Reaction Steps

1 g (2.76 mmol) of 4-(m-chloroanilino)-5,6-dimethyl-7-benzyl-pyrrolo[2,3-d]pyrimidine and 2.57 g (19.32 mmol) of AlCl3 are heated at reflux in 20 ml of toluene for 2 hours, until all starting material has disappeared in a TLC. The reaction solution is cooled to RT, poured onto ice-water and stirred at 0° C. for 2 hours. The precipitate is filtered off with suction and dissolved in hot ethyl acetate. The ethyl acetate solution is washed twice each with 5% sodium hydrogen carbonate solution and sat. NaCl solution, is dried and is concentrated by evaporation. The residue is crystallised from ethyl acetate/hexane, yielding 4-(m-chloroanilino)-5,6-dimethyl-7H-pyrrolo[2,3-d]pyrimidine in the form of colourless crystals having a melting point of 239°-240° C.

Provenance & Evidence