Dimethyl Sulfate → 5-(benzyloxy)-2-(2-chloropyridin-4-yl)-3-methylpyrimidin-4(3H)-one

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Reaction Steps

To a mixture of 5-(benzyloxy)-2-(2-chloropyridin-4-yl)pyrimidin-4-ol (14.2 g, 112 mmol), Cs2CO3 (36.6 g, 112 mmol) in 300 mL of 1,4-dioxane, was added Me2SO4 (17.6 g, 56 mmol) and the resulting mixture was refluxed for 5 min. After cooling to rt, EtOAc (300 mL) and water (200 mL) were added. The organic layer was separated, the aqueous layer was extracted with EtOAc (2×100 mL). The combined organic layer was washed with water, brine, and dried over Mg2SO4, filtered, and concentrated to give 25 g of crude compound, which was purified by silica gel to afford 5-(benzyloxy)-2-(2-chloropyridin-4-yl)-3-methylpyrimidin-4(3H)-one (4.0 g, 22%). 1H-NMR δ (400 MHz, d6-DMSO): 8.53 (dd, J=5.2, 0.4 Hz, 1H), 7.51 (s, 1H), 7.44 (m, 3H), 7.42-7.29 (m, 4H), 5.19 (s, 2H), 3.33 (s, 3H); MS (ESI) m/z (M+H)+ 328.

Provenance & Evidence