Water → 4-(4-Methylpent-1-ynyl)-2-(methylthio)pyrimidine

Participants

Reaction Steps

To a cold (0° C.) solution of 4-iodo-2-(methylthio)pyrimidine (4.73 g, 21.2 mmol) in tetrahydrofuran (70 mL) was added copper (I) iodide (404 mg, 2.12 mmol), dichlorobistriphenylphosphine palladium (II) (744 mg, 1.06 mmol), and triethylamine (8.8 mL, 63.8 mmol). 4-Methyl-pentyne (5.0 mL, 42.5 mmol) was added dropwise to the reaction mixture and the resultant solution was stirred at 0° C. for 30 minutes and then at room temperature for 72 hours. Water and ether were added and the layers separated. The organic layer was washed with brine. The aqueous layer was extracted with ether and the combined organics were dried over magnesium sulfate. Filtration and concentration followed flash chromatography on silica gel (4:1 hexane-ether) provided 4-(4-methylpent-1-ynyl)-2-(methylthio)pyrimidine (4.0 g, 92%) as a clear oil. 1H NMR (CDCl3) δ 8.44 (d, 1H), 6.96 (d, 1H), 2.56 (s, 3H), 2.35 (d, 2H), 1.97 (M, 1H), 1.05 (d, 6H); MS m/z 207 (M+1).

Provenance & Evidence