The mixture of 5-bromo-N-(5-cyclopropyl-1H-pyrazol-3-yl)-2-phenylpyrimidin-4-amine (0.3 g, 0.84 mmol, 1.0 equiv.), (E)-tributyl(prop-1-enyl)stannane (0.5 g, 1.5 mmol, 1.5 eq), Bu4NBr (0.32 g, 0.84 mmol, 1.0 eq), Pd(PPh3)2Cl2 (0.1 g, 0.034 mmol, 0.04 eq) and dioxane (10 mL) was heated to reflux for 18 h. Then, silica gel was added to the reaction mixture and evaporated to dry. The residue was purified by silica gel chromatography (hexane/EtOAc/Et3N=100:100:1 as eluent) to generate (E)-N-(5-cyclopropyl-1H-pyrazol-3-yl)-2-phenyl-5-(prop-1-enyl)pyrimidin-4-amine (Compound 11) (0.1 g, 37.5%). LC-MS (m/z): 357.2 [M+H]+. 1H NMR (300 MHz, DMSO-d6): δ 0.71-0.72 (m, 2H), 0.94-1.02 (m, 2H), 1.74-1.80 (m, 3H), 1.87-1.96 (m, 1H), 5.98 (d, J=11.4 Hz, 1H), 6.48 (d, J=11.4 Hz, 1H), 7.47-7.49 (m, 3H), 8.24-8.32 (m, 2H), 8.71 (s, 1H), 12.12 (s, 1H).
