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. Author manuscript; available in PMC: 2015 Mar 13.
Published in final edited form as: J Med Chem. 2013 Nov 6;57(5):1914–1931. doi: 10.1021/jm401329s

Scheme 5. Synthesis of 2,4,7-trisubstituted quinazoline core.

Scheme 5

Reagents and conditions: (a) Pivaloyl chloride, Et3N, CH2Cl2; (b) aq. NaOH, EtOH, reflux, 52% two steps; (c) 4-(methanesulfonamido)phenylboronic acid, Pd(PPh3)4, Na2CO3, MeOH, toluene, 115 °C, 84%; (d) POCl3, DIPEA, benzene, reflux, 87%.