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. 2022 Sep 27;65(19):13172–13197. doi: 10.1021/acs.jmedchem.2c00996

Scheme 3. Convergent Synthesis Leading to 4- and 5-Substituted Pyrimidine Analogues of IKK16.

Scheme 3

Reagents and conditions: (a) 4-(pyrrolidin-1-yl)piperidine, HATU, TEA, DMF, rt, and 80%; (b) 4 M HCl/dioxane, DCM, rt, and 67%; (c) Pd(PPh3)4, boronic acid, Na2CO3, toluene/EtOH/water (or dioxane/water), 70 °C, and 8–66%; (d) 2-(tributylstannyl)thiazole, Pd(Ph3P)4, LiCl, DMF, 70 °C, and 10%; (e) TFA, 2,2,2-trifluoroethanol, μW, 140 °C, and 8–64%; and (f) Pd(OAc)2, BINAP, Cs2CO3, dioxane, 80 °C, and 9–19%.