Example 12: Synthesis of 4-chloro-6-(methylthio)pyrimidine. 4,6-Dichloropyrimidine (15.4 g, 0.10 mol) was dissolved in THF (120 mL) at room temperature, followed by the addition of solid sodium methanethiol (NaSMe, 8.5 g, 0.12 mol). The reaction mixture was heated to 60 °C and maintained for 16 hours. After completion of the reaction, the mixture was cooled to room temperature and diluted with ethyl acetate (300 mL) and water (300 mL). The organic layer was separated, washed with brine, dried over anhydrous sodium sulfate and concentrated to give an orange colored oil. Recrystallization by hexane gave the light yellow solid product 4-chloro-6-(methylthio)pyrimidine (9.85 g, 0.061 mol, 61% yield).1H NMR (500 MHz, CDCl3) δ: 8.74 (s, 1H), 7.23 (s, 1H), 2.58 (s, 3H).
