Hydrogen iodide → 4-Iodo-2-methyl-6-(methylthio)pyrimidine

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A mixture of 4-chloro-2-methyl-6-(methylthio)pyrimidine (5.3 g, 30.3 mmol) and hydriodic acid (67% solution, 5.71 mL, 76 mmol, Alfea Aesar, Avocado, Lancaster) in DCM (20 mL) was stirred at room temperature for 20 h and filtered. The collected solid was washed with DCM and then suspended in saturated NaHCO3 and extracted with EtOAc (2×). The combined organic extracts were washed with brine, dried over Na2SO4, and concentrated to give 4-iodo-2-methyl-6-(methylthio)pyrimidine (7.3 g, 27.4 mmol, 90% yield) as a light yellow solid. 1H NMR (400 MHz, CDCl3) δ 7.43 (s, 1H); 2.62 (s, 3H); 2.52 (s, 3H). m/z (ESI, +ve ion) 266 (M+H)+.

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