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

Participants

Reaction Conditions

Reaction Steps

Under a nitrogen atmosphere, 261 mg (1.00 mmol) of 3-amino-4-(3-chlorophenylamino)-1 H-pyrazolo[3,4-d]pyrimidine (see Step 1.6), 273 mg (1.5 mmol) of biphenyl-4-carbaldehyde and 180 mg of acetic acid are stirred in 39 ml of DMEU/methanol (1:2) at RT for 1 hour. 440 mg (7 mmol) of NaCNBH3 are then added and the reaction mixture is heated to 50° C. After 15 hours a further 440 mg of NaCNBH3 are added and the reaction mixture is stirred at boiling temperature for 15 hours, then poured into 0.6 liter of a 1% aqueous K2B4O7.4H2O solution and stirred overnight to complete the reaction. The precipitated product is filtered off and washed with water. Heating in 20 ml of ethanol and filtration yield 4-(3-chloro-phenylamino)-3-(4-phenyl-benzylamino)-1H-pyrazolo[3,4-d]pyrimidine; m.p. 250-252° C.; HPLC: tRet(grad20-100/20=14.1; FAB-MS: (M+H)+=427.

Provenance & Evidence