Water → 2-Pyrimidineacetic acid ethyl ester

Participants

Reaction Steps

A solution of diethyl 2-(pyrimidin-2-yl)malonate (1.0 g, 4.2 mmol) and sodium chloride (491 mg, 8.4 mmol) in DMSO (6 ml) and water (151 μl, 8.4 mmol) was heated at 180° C. for 20 min. The mixture was cooled to room temperature, water (12 ml) was added, and the solution extracted with EtOAc (2×20 ml). The combined organic layers were dried (MgSO4) and evaporated. The residue was chromatographed on silica, eluting with hexane:EtOAc (2:1), to afford the ester (434 mg, 62%) as a pale yellow oil. 1H NMR (250 MHz, CDCl3) δ 1.27 (3H, t, J=7.1 Hz), 4.04 (2H, s), 4.23 (2H, q, J=7.1 Hz), 7.22 (1H, t, J=5.3 Hz), 8.72 (2H, d, J=5.3 Hz).

Provenance & Evidence