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 coppercatalyzed iV-arylation of heteroarylamme 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 N2H 4.H2O/FeCl3/C system using water as a solvent in good yield. © 2008 American Chemical Society.
CITATION STYLE
Liu, Y. F., Wang, C. L., Bai, Y. J., Han, N., Jiao, J. P., & Qi, X. L. (2008). A facile total synthesis of imatinib base and its analogues. Organic Process Research and Development, 12(3), 490–495. https://doi.org/10.1021/op700270n
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