Methyl iodide → HCID 66634531, compound

Participants

Reaction Steps

An ice-cold solution of 1-[5-(5-fluoro-pyridin-3-yl)-[1,3,4]thiadiazol-2-yl]-1-methyl-3-(2-methylsulfanyl-ethyl)-urea (0.132 g, 0.4 mmol) in N,N-dimethylformamide (0.6 mL) was treated with sodium hydride (60% in mineral oil, 0.018 g, 0.4 mmol) and stirred for 5 minutes before addition of a solution of iodomethane (0.063 g, 0.4 mmol) in N,N-dimethylformamide (0.1 mL). The ice bath was removed after 5 minutes. The reaction mixture was stirred at room temperature for 14 hours, diluted with water (30 mL) and extracted with EtOAc (3×20 mL). The combined organic extracts were washed with brine (20 mL), dried over MgSO4, purified by normal and reversed phase chromatography to give the title compound as a colorless gum (0.027 g, 20%): IR (KBr thin film) 1658 cm−1; 1H NMR (400 MHz, CDCl3) δ 8.87 (s, 1H), 8.53 (d, J=3.2 Hz, 1H), 8.02 (ddd, J=9.1, 4.5, 1.7 Hz, 1H), 3.66 (s, 3H), 3.59 (t, J=6.8 Hz, 2H), 3.06 (s, 3H), 2.78 (t, J=7.1 Hz, 2H), 2.14 (s, 3H); ESIMS m/z 342 ([M+H]+).

Provenance & Evidence