Acetic Acid → 4-(3-chloro-phenylamino)-3-[(3-methoxy-4-hydroxy-benzyl)-amino]-1H-pyrazolo[3,4-d]pyrimidine

Participants

Reaction Steps

228 mg (1.50 mmol) of 4-hydroxy-3-methoxy-benzaldehyde are added (N2 atmosphere) 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, 26 ml of DMEU and 120 mg (2.0 mmol) of acetic acid. After 1 hour, 440 mg (7.0 mmol) of NaCNBH3 are added to the clear solution and stirring is then carried out at RT for 7 days. The reaction solution is poured into 0.8 liter of water and stirred overnight to complete the reaction, during which time the product precipitates. Filtering with suction, washing with water, stirring in hot ethyl acetate, cooling and filtering yield 4-(3-chloro-phenylamino)-3-[(3-methoxy-4-hydroxy-benzyl)-amino]-1H-pyrazolo[3,4-d]pyrimidine; m.p. 223-225° C.; HPLC: TRet (Grad5-40)=19.8; FAB-MS: (M+H)+ =397.

Provenance & Evidence