Triethylamine → HCID 18446615, compound

Participants

Reaction Steps

4-Iodo-2-(methylsulfanyl)pyrimidine (1.76 g, 7.1 mmol) was dissolved in anhydrous tetrahydrofuran (50 mL). To this solution was added triethylamine (1.2 mL, 8.5 mmol), copper (I) iodide (70 mg, 0.4 mmol) and dichlorobis(triphenylphosphine)palladium (II) (150 mg, 0.21 mmol). A solution of 4-ethynyl-2-(methylsulfanyl)pyrimidine (1.0 g, 7.1 mmol) in tetrahydrofuran was added dropwise. The reaction mixture was stirred at room temperature overnight Ethyl acetate and water were added to the reaction mixture. The phases were separated and the aqueous phase extracted with additional ethyl acetate. The organics were combined, dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography (1:1 ethyl acetate:hexane) gave 1.35 g (69%) of 2-(methylsulfanyl)-4-{[2-(methylsulfanyl)-4-pyrimidinyl]ethynyl}pyrimidine as a white solid. 1H NMR (CDCl3): δ 8.57 (d, 2H), 7.19 (d, 2H), 2.59 (s, 6H); MS m/z 275 (M+1).

Provenance & Evidence