Methyl iodide → HCID 57550065, compound

Participants

Reaction Steps

To a stirring suspension of sodium hydride (9.1 mg, 0.23 mmol), N-(4-(2-oxo-4-(1-(5-propylpyrimidin-2-yl)piperidin-4-yloxy)pyridin-1(2H)-yl)phenyl)pivalamide (15 mg, 0.030 mmol) in DMF (2 mL) was added Methyl iodide (10 μL, 0.16 mmol). The reaction was stirred at room temperature for 1.5 h. The reaction was quenched with H2O and extracted with EtOAc. The organic layer was concentrated in vacuo to a white solid. The solid was purified by flash chromatography (SiO2, 0 to 100% EtOAc in CH2Cl2) to yield 10 mg of the desired product as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 8.19 (s, 2 H), 7.39-7.48 (m, 2 H), 7.32-7.39 (m, 2 H), 7.26 (d, J=2.01 Hz, 1H), 5.98-6.09 (m, 2 H), 4.55-4.64 (m, 1 H), 4.16-4.28 (m, 2 H), 3.59-3.71 (m, 2H), 3.27 (s, 3 H), 2.43 (t, J=7.40 Hz, 2 H), 1.98-2.22 (m, 2 H), 1.74-1.98 (m, 2 H), 1.53-1.66 (m, 2 H), 1.12 (s, 9 H), 0.96 (t, J=7.28 Hz, 3 H). MS (ESI) 504 (M+H).

Provenance & Evidence