Diethyl Ether → HCID 178437119, compound

Participants

Reaction Steps

To a mixture of crude 4-(bromomethyl)-3,5-diethylpyridine and 2-sulfanyl-6-(trifluoromethyl)pyrimidin-4-ol (0.838 g, 5.89 mmol) in anhydrous ethanol (50 mL) at 0° C. was added triethylamine (3.21 g, 4.42 mL, 31.75 mmol). The reaction mixture was allowed to stir at room temperature overnight. The solvent was evaporated to provide a crude residue. Ether was added to precipitate the triethylamine hydrobromide salt. The solid was filtered and washed with ether several times. The combined ether layers were evaporated, and the crude residue was purified by Combiflash using 0-10% MeOH in dichloromethane to provide 2-{[(3,5-diethylpyridin-4-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol and 2-{[(3-ethylpyridin-4-yl)methyl]sulfanyl}-6-methylpyrimidin-4-ol as a white solid; 1H NMR (400 MHz, DMSO-d6): δ 1.19 (t, 6H), 2.64 (q, 4H), 4.55 (s, 2H), 6.70 (s, 1H), 8.30 (s, 2H); M+1 344.4.

Provenance & Evidence