Acetic Acid → HCID 178490497, compound

Participants

Reaction Steps

788 mg (4.8 mmol) of 4-formyl-benzoic acid methyl ester and 300 mg of 5% Pt/C are added to a solution of 1.04 g (4.0 mmol) of 3-amino-4-(3-chloro-phenylamino)-1H-pyrazolo[3,4-d]pyrimidine in 40 ml of DMEU and 961 mg (16 mmol) of acetic acid and hydrogenation is carried out immediately (instead of hydrogenation, reduction with NaCNBH3 is also possible). After two days and after four days, a further 788 mg of 4-formylbenzoic acid methyl ester is added. After 7 days the catalyst is separated off from the reaction mixture by filtration through Celite, the filtrate is decolorized by treatment with activated carbon and then concentrated by evaporation under a high vacuum at 70° C. to give a residue of ≈4 g. Crystallization with diisopropyl ether/toluene yields product of ≈80% purity. Heating in a mixture of 30 ml of ethanol and ≈5 ml of acetone, filtering while hot, concentration by evaporation to half the volume and cooling yield 4-(3-chloro-phenylamino)-3-(4-methoxy-carbonylbenzylamino)-1H-pyrazolo[3,4-d]pyrimidine; m.p. 228° C.; FAB-MS: (M+H)+ =409.

Provenance & Evidence