220041-42-9

149849-92-3

75-65-0

220041-42-9

A suspension of 2-chloropyrimidine-4-carboxylic acid (0.501 g) was added to a 100 mL round bottom flask under nitrogen protection, followed by pyridine (3 mL, 37.1 mmol) and p-toluenesulfonyl chloride (1.196 g, 6.27 mmol). Tert-butanol (20 mL, 209 mmol) was added to the mixture and the reaction mixture was stirred at room temperature for 16 hours. Upon completion of the reaction, the reaction solution was neutralized by slow addition of saturated aqueous sodium bicarbonate and the mixture was subsequently concentrated under reduced pressure. Water was added to the concentrate to induce precipitate formation, the precipitate was collected by filtration and the filter cake was washed with water. The resulting wet solid was processed by freeze drying to afford tert-butyl 2-chloropyrimidine-4-carboxylate (0.526 g, 78% yield) as a light beige solid. HPLC (Analytical Method A) retention time: 1.735 min. 1H NMR (400 MHz, CDCl3) δ 8.83 (d, J = 5.1 Hz, 1H), 7.85 (d, J = 4.7 Hz, 1H), 1.64 (s, 9H).