Toluene → HCID 178516287, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 200 mg (0.537 mmol) of 3(3-aminomethyl-phenylamino)-4-(3-chloro-phenylamino)-1H-pyrazolo[3,4-d]pyrimidine (water content: 1.79%; see Step 90.5) and 10 ml of toluene is concentrated by evaporation in vacuo for the purpose of removing water and, after repetition of that operation, the residue is taken up in 10 ml of toluene. After the addition of 59 mg (0.59 mmol) of succinic anhydride and 0.082 ml (0.59 mmol) of triethylamine, the reaction mixture is heated for 1 hour at 80° C. and for 18 hours under reflux. A further 21 mg (0.21 mmol) of succinic anhydride and 0.041 ml (0.2949 mmol) of triethylamine are added to the reaction mixture which is heated for a further 6 hours under reflux, then cooled to room temperature and 10 ml of diethyl ether are added. Filtration, purification of the filter residue by flash chromatography (silica gel having a particle size of 0.04-0.06 mm; eluant: ethyl acetate), concentration of the product-containing fractions by evaporation in vacuo and recrystallization of the residue from methanol yield 4-(3-chloro-phenylamino)-3-(3-[succinimido-methyl]-phenylamino)-1H-pyrazolo[3,4-d]pyrimidine having a water content of 7.72%; m.p. 140-142° C.; ESI-MS: (M−H)−=446.

Provenance & Evidence