Methyl Methanesulfonate → 5-Fluoro-4-imino-1-methyl-1,4-dihydropyrimidin-2-ol

Participants

Reaction Conditions

Reaction Steps

A 25 mL screw-top vial was charged with 4-amino-5-fluoropyrimidin-2-ol (151.0 mg, 1.17 mmol), K2CO3 (289.2 mg, 2.09 mmol), 18C6 (278.6 mg, 0.901 mmol) and anhydrous DMF (10 mL). Methyl methanesulfonate (0.0814 mL, 0.961 mmol) was added, and the resulting mixture was agitated on a rotary shaker at 85° C. for 21 h. After cooling to room temperature, the crude material was concentrated in vacuo and purified by reverse phase column chromatography to afford 4-amino-5-fluoro-1-methylpyrimidin-2(1H)-one (61.9 mg, 37%) as a beige solid: mp 195° C. (dec.); 1H NMR (400 MHz, DMSO-d6) δ 7.94 (d, J=6.8 Hz, 1H), 7.52 (s, 1H), 7.32 (s, 1H), 3.18 (s, 3H); ESIMS m/z 144 ([M+H]+.

Provenance & Evidence