p-Toluenesulfonic acid → HCID 22125017, compound

Participants

Reaction Steps

A mixture of 700 mg (2.9 mmol) of 4-phenylamino-2-methylthiopyrimidine-5-carboxaldehyde, 490 mg (3.0 mmol) of 2,6-dichloroaniline and 100 mg (0.5 mmol) of 4-toluenesulfonic acid in 50 ml of toluene was heated at reflux with the azeotropic removal of water for 18 hours. The mixture was cooled and evaporated. 50 ml of methanol and 400 mg (11.7 mmol) of sodium borohydride were added and the mixture was heated at reflux for 20 minutes, cooled and then evaporated. The residue was stirred in a mixture of 50 ml of 2M aqueous sodium hydroxide and 50 ml of ethyl acetate for 30 minutes and then the phases were separated. The organic phase was dried over magnesium sulfate, filtered and evaporated. Flash chromatography of the residue on silica gel using diethyl ether/hexane (2:3) for the elution gave 410 mg (36%) of 5-(2,6-dichlorophenyl)aminomethyl-4-phenylamino-2-methylthiopyrimidine as a white solid.

Provenance & Evidence