3-Chloro-4-Methyl-1,8-naphthyridine synthesis

Yield:893566-38-6 52%

Reaction Conditions:

Stage #1: N-(5-chloro-4-methylpyridin-2-yl)pivalamidewith tert.-butyl lithium in diethyl ether at -65 - -15;Inert atmosphere;
Stage #2: 3-dimethylaminoacrolein in diethyl ether at -15 - 20;Inert atmosphere;

References:

Magee, Thomas V.;Ripp, Sharon L.;Li, Bryan;Buzon, Richard A.;Chupak, Lou;Dougherty, Thomas J.;Finegan, Steven M.;Girard, Dennis;Hagen, Anne E.;Falcone, Michael J.;Farley, Kathleen A.;Granskog, Karl;Hardink, Joel R.;Huband, Michael D.;Kamicker, Barbara J.;Kaneko, Takushi;Knickerbocker, Michael J.;Liras, Jennifer L.;Marra, Andrea;Medina, Ivy;Nguyen, Thuy-Trinh;Noe, Mark C.;Obach, R. Scott;O'Donnell, John P.;Penzien, Joseph B.;Reilly, Usa Datta;Schafer, John R.;Shen, Yue;Stone, Gregory G.;Strelevitz, Timothy J.;Sun, Jianmin;Tait-Kamradt, Amelia;Vaz, Alfin D. N.;Whipple, David A.;Widlicka, Daniel W.;Wishka, Donn G.;Wolkowski, Joanna P.;Flanagan, Mark E. [Journal of Medicinal Chemistry,2009,vol. 52,# 23,p. 7446 - 7457] Location in patent:experimental part