Acetic Acid → 4-(3-chloro-phenylamino)-3-[3-(methylaminocarbonyl)-benzylamino]-1H-pyrazolo[3,4-d]pyrimidine

Participants

Reaction Steps

A solution of 261 mg (1.0 mmol) of 3-amino-4-(3-chloro-phenylamino)-1H-pyrazolo[3,4-d]pyrimidine (see Step 15.1) and 245 mg (1.5 mmol) of 3-(methylamino-carbonyl)-benzaldehyde in 26 ml of methanol, 26 ml of DMEU and 180 mg (3.0 mmol) of acetic acid is stirred for 1 hour at RT. Then 440 mg (7.0 mmol) of NaCNBH3 are added and the reaction mixture is stirred for 9 days at RT. The methanol is evaporated off from the reaction solution using a rotary evaporator, the residue is poured into 0.6 liter of water and stirring is carried out overnight. The product precipitates. Filtering with suction, washing with water, stirring twice in 10 ml of boiling ethanol, cooling and filtering yield 4-(3-chloro-phenylamino)-3-[3-(methylaminocarbonyl)-benzylamino]-1H-pyrazolo[3,4-d]pyrimidine; m.p. 252-254° C.; HPLC: TRet (Grad5-40)=16.9; FAB-MS: (M+H)+ =408.

Provenance & Evidence