Sodium Hydroxide → 5-Bromo-5-(2-ethoxy-ethyl)-pyrimidine-2,4,6-trione

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Reaction Steps

To a mixture of 5-(2-ethoxy-ethyl)-pyrimidine-2,4,6-trione (27.8 g, 139 mmol) (from Preparation 2A) and 1.5 L of water was added 1M sodium hydroxide solution (140 mL) and bromine (7.2 mL, 22.2 g, 139 mmol) at 0° C. After warming to room temperature, the mixture was stirred for 48 hours, filtered, and the solids were washed with water, then ether, then hexanes and dried in vacuo, afforidng 23 g of 5-bromo-5-(2-ethoxy-ethyl)-pyrimidine-2,4,6-trione. 1H NMR (CDCl3): 8.37 (bs, 2H), 3.53 (t, 2H, J=7.0 Hz), 3.35 (q, 2H, J=6.5 Hz), 2.99 (t, 2H, J=7.0 Hz), 1.05 (t, 3H, J=6.5 Hz) ppm. MS (m/z, APCI): 468 [M+H]+.

Provenance & Evidence