Chloroacetic Acid → 2-(6-Oxo-1,6-dihydropyrimidin-1-yl)acetic acid

Participants

Reaction Conditions

Reaction Steps

To pyrimidin-4(3H)-one (0.608 g, 6.33 mmol) was added 5 N sodium hydroxide solution (2.5 ml) followed by chloroacetic acid (0.598 g, 6.33 mmol). The reaction mixture was heated at 105° C. for 2 h. After cooling to ambient temperature, the reaction was neutralized with 2 N hydrochloric acid (3.2 ml) and then directly purified by reverse phase HPLC (TMC Pro-Pac C18; 0-40% 0.1% trifluoroacetic acid in acetonitrile/0.1% trifluoroacetic acid in water gradient). Removal of the volatiles in vacuo afforded the title compound as a white solid. 1H NMR (DMSO-d6): δ 13.2 (s, 1H), 8.43 (s, 1H), 7.94 (d, J 6.7 Hz, 1H), 6.43 (d, J=6.6 Hz, 1H), 4.63 (s, 2H). LC/MS 155.1 (M+1)+.

Provenance & Evidence