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A Facile Total Synthesis of Imatinib Base and Its Analogues

2008; American Chemical Society; Volume: 12; Issue: 3 Linguagem: Inglês

10.1021/op700270n

1520-586X

Yifeng Liu, Cuiling Wang, Yajun Bai, Ning Han, Junping Jiao, Xiaoli Qi,

Click Chemistry and Applications

Imatinib and its analogues were successfully synthesized by an improved method in 19.5– 46.2% total yield of six main steps. Pyrimidinyl amine was prepared by the reaction of enaminone and guanidine nitrate without the use of a toxic cyanamide. N-(2-Methyl-5-nitrophenyl)-4-(pyridin-3-yl) pyrimidin-2-amine as a key intermediate for the synthesis of imatinib was prepared by copper-catalyzed N-arylation of heteroarylamine in 82% yield. The copper salts were used instead of the expensive palladium compounds in this C−N bond-forming reaction. The intermediate nitro compound was reduced by a N2H4·H2O/FeCl3/C system using water as a solvent in good yield.