Acetic Acid → HCID 19610585, compound

Participants

Reaction Steps

225 mg (1.50 mmol) of 3-formyl-benzoic acid are added to a solution of 261 mg (1.00 mmol) of 3-amino-4-(3-chloro-phenylamino)-1H-pyrazolo[3,4-d]pyrimidine in 26 ml of methanol, 13 ml of DMEU and 120 mg (2.0 mmol) of acetic acid under a N2 atmosphere. The reaction mixture is stirred for 1 hour, during which time a solid precipitates, and then 440 mg (7.0 mmol) of NaCNBH3 are added. Stirring is carried out for 5 days, the suspension changing to a clear solution. The methanol is evaporated off using a rotary evaporator. The residue is poured into 0.6 liter of water and stirred for 3 hours to complete the reaction. Filtering with suction, washing with water and diethyl ether, stirring in hot ethanol, cooling and filtering yield 3-(3-carboxy-benzylamino)-4-(3-chloro-phenylamino)-1H-pyrazolo[3,4-d]pyrimidine (3-{[4-(3-chloro-phenylamino)-1H-pyrazolo[3,4-d]pyrimidin-3-yl-amino]methyl}-benzoic acid); m.p. 294-296° C.; HPLC: TRet (Grad5-40)=20.1; FAB-MS: (M+H)+ =395.

Provenance & Evidence