Water → HCID 67508203, compound

Participants

Reaction Steps

A solution of 5-chloro-4-iodo-2-(methylthio)pyrimidine (5 g, 17.4 mmol) and Pd(PPh3)4 (1 g, 0.87 mmol) in dry THF (120 mL) was degassed under N2 three times. Then a solution of (3-methylpyridin-2-yl)zinc(II) bromide in THF (0.5 M, 53 mL, 26.3 mmol) was added. The resulting mixture was heated at reflux overnight. The mixture was then cooled to room temperature and was treated with EtOAc (80 mL) and H2O (100 mL). The layers were separated and the aqueous layer was extracted with EtOAc (50 mL×3). The combined organic layers were washed with brine (50 mL), dried over Na2SO4 and filtered. The filtrate was concentrated and filtered. The filtrate was concentrated and the residue was purified via column chromatography (petroleum ether: EtOAc=9:1) to give the title compound (2.8 g, 64%) as a yellow syrup.

Provenance & Evidence