Water → 2-amino-N-[2-[4-[[9-[(4-fluorophenyl)methyl]-9H-purin-8-yl]amino]-1-piperidinyl]ethyl]benzamide (E)-2-butenedioate

Participants

Reaction Conditions

Reaction Steps

A mixture of 1.4 parts of 2H-3,1-benzoxazine-2,4-(1H)-dione, 3.7 parts of N-[1-(2-aminoethyl)-4-piperidinyl]-9-[(4-fluorophenyl)methyl]-9H-purin-8-amine and 45 parts of N,N-dimethylformamide was stirred for 4 hours at 70° C. After cooling, the reaction mixture was poured into water and the product was extracted with 4-methyl-2-pentanone. The extract was washed with water, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia, (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was converted into the (E)-2-butenedioate salt in ethanol. The salt was filtered off and dried, yielding 4.3 parts (50%) of 2-amino-N-[2-[4-[[9-[(4-fluorophenyl)methyl]-9H-purin-8-yl]amino]-1-piperidinyl]ethyl]benzamide (E)-2-butenedioate(2:5): mp. 164° C. (compound 178).

Provenance & Evidence