Methyl iodide → HCID 86267585, compound

Participants

Reaction Steps

A suspension of Example 7 (0.050 g, 0.12 mmol) in acetone (2.5 mL) was treated with Cs2CO3 (0.080 g, 0.25 mmol) and iodomethane (0.02 mL, 0.32 mmol) and the mixture was stirred at RT for 12 h. The solvent was removed in vacuo and the residue was dissolved in DCM (3 mL) and washed with water (3 mL). The aqueous phase was extracted with DCM (4×5 mL) and the combined organics were dried (MgSO4) and concentrated in in vacuo. The residue was triturated with Et2O (2 mL) and sonicated for 5 min, which lead to the precipitation of an off white solid. Solid was isolated by filtration and washed with Et2O (3×1 mL). The solid was dried under high vacuum for 3 h, and was then dissolved in MeCN and water, frozen to −78° C., and lyophilized to afford 3-(tert-butyl)-4-methyl-1-(6-methyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)-1H-1,2,4-triazol-5(4H)-one (0.024 g, 46.4%) as an off white solid. 1H NMR (400 MHz, DMSO-d6): δ 8.37 (d, J=5.7 Hz, 1H), 8.26 (s, 1H), 7.96 (s, 1H), 7.85 (d, J=8.7 Hz, 1H), 7.72 (d, J=8.7 Hz, 1H), 7.20 (d, J=2.4 Hz, 1H), 6.65 (dd, J=5.7, 2.4 Hz, 1H), 3.84 (s, 3H), 3.39 (s, 3H), 2.34 (s, 3H), 1.37 (s, 9H); MS (ESI) m/z: 420.2 (M+H+).

Provenance & Evidence