Benzyl Bromide → HCID 58487941, compound

Participants

Reaction Steps

In a 20 mL microwave vial, 5-fluoro-4-imino-1-(4-methoxyphenylsulfonyl)-3,4-dihydropyrimidin-2(1H)-one (111 mg, 0.37 mmol) was stirred at room temperature in dimethyl formamide (3 mL) together with anhydrous potassium carbonate (210 mg, 0.55 mmol). Benzylbromide (89 μL, 0.75 mmol) was added. The reaction was capped and placed on a Biotage Initiator microwave reactor for 20 min at 130° C., with external IR-sensor temperature monitoring from the side of the vessel. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (EtOAc; 250 mL), and washed with water (H2O; 3×100 mL). The organic phase was dried over magnesium sulfate (MgSO4), filtered, and the solvent evaporated under reduced pressure. Purification by flash chromatography (SiO2, EtOAc/Hexanes gradient) afforded 3-benzyl-5-fluoro-4-imino-1-(4-methoxyphenylsulfonyl)-3,4-dihydropyrimidin-2(1H)-one as a pale yellow oil (15 mg; 11%): 1H NMR (400 MHz, CDCl3) δ 8.09-8.02 (m, 3H), 7.38-7.27 (m, 6H), 7.00-6.96 (m, 2H), 4.65 (d, J=5.7 Hz, 2H), 3.87 (s, 3H). ESIMS m/z 391 ([M+H]+).

Provenance & Evidence