Hydrochloric Acid → (2-Aminopyrimidin-5-yl)boronic acid

Participants

Reaction Conditions

Reaction Steps

To a mixture of [2-[(tert-butoxycarbonyl)amino]pyrimidin-5-yl]boronic acid 12 (40.0 kg, 49 wt % by HPLC, 82.0 mol) in water (245 kg) was added concentrated hydrochloric acid (39.6 L) while maintaining the temperature below 30° C. The reaction mixture was stirred for 12 h and was then cooled to 10° C. The pH of the mixture was adjusted to 6.5 by addition of 50% aqueous sodium hydroxide solution while maintaining the temperature below 15° C. and the mixture was then stirred for 1 h. Water (69.0 kg) was added and the mixture was aged for 30 min. The resulting slurry was filtered and the cake was dried under vacuum at 50° C. to afford 2-aminopyrimidin-5-ylboronic acid III (10.2 kg, 90% yield). 1H NMR (300 MHz, DMSO-d6) δ 8.50 (s, 2H), 7.97 (s, 2H), 6.74 (s, 2H).

Provenance & Evidence