Skip to main content
. 2021 Jul 15;64(15):10849–10877. doi: 10.1021/acs.jmedchem.0c02274

Scheme 9. Synthesis of Thieno[3,2-d]pyrimidine and Thieno[2,3-d]pyrimidine Hinge Binders.

Scheme 9

Reagents and conditions: (a) 3, Pd(PPh3)4, Cs2CO3, dioxane/water, 125 °C, μW, 15 min; (b) PhB(OH)2, NaHCO3, CsF, Pd(PPh3)4, dioxane/H2O, 95 °C, 3 h; (c) 3, Pd(PPh3)4, Cs2CO3, dioxane/water, 125 °C, 15 min; (d) 3, Pd(PPh3)4, Cs2CO3, dioxane/water, 125 °C, μW, 15 min; (e) 4, Pd(PPh3)4, Cs2CO3, dioxane/water, 145 °C, μW, 15 min; (f) PhB(OH)2, NaHCO3, CsF, Pd(PPh3)4, dioxane/H2O, 80 °C, 4 h; (g) aq LiOH, dioxane, 100 °C, 16 h, then aq HCl.