Potassium Carbonate → HCID 136387348, compound

Participants

Reaction Conditions

Reaction Steps

3-(tert-Butyl)-1-(5-((6-chloropyrimidin-4-yl)oxy)-6-methylpyridin-2-yl)-1H-1,2,4-triazol-5(4H)-one (0.10 g, 0.28 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.08 g, 0.36 mmol), and K2CO3 (0.10 g, 0.72 mmol) were suspended in a solution of dioxane (2.5 mL) and water (0.50 mL). The suspension was sonicated and sparged with Ar for 10 min. Pd(PPh3)4 (0.032 g, 0.028 mmol) was added and the reaction mixture was stirred at 85° C. for 16 h. The mixture was diluted with sat. NH4Cl (aq) 5 mL) and the resultant emulsion was extracted with EtOAc (4×10 mL). The combined organics were dried (Na2SO4) and concentrated in vacuo. The residue was purified by silica gel chromatography (MeOH/DCM) to afford a brown amorphous solid that was triturated with MeCN (1.5 mL). A white precipitate formed following sonication and was isolated by filtration and dried to afford 3-(tert-butyl)-1-(6-methyl-5-((6-(1-methyl-1H-pyrazol-4-yl)pyrimidin-4-yl)oxy)pyridin-2-yl)-1H-1,2,4-triazol-5(4H)-one (0.055 g, 48.3%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 11.95 (s, 1H), 8.61 (d, J=1.1 Hz, 1H), 8.48 (s, 1H), 8.17 (s, 1H), 7.80 (d, J=8.7 Hz, 1H), 7.73 (d, J=8.7 Hz, 1H), 7.46 (d, J=1.1 Hz, 1H), 3.89 (s, 3H), 2.29 (s, 3H), 1.27 (s, 9H); MS (ESI) m/z: 420.3 (M+H+).

Provenance & Evidence