2-Aminopyridine → HCID 86615861, compound

Participants

Reaction Conditions

Reaction Steps

Part A: To a solution of 2-aminopyridine (9.41 g, 100 mmol) in methylene chloride (200 mL) at 25° C. was added thiocarbonyl diimidazole (18.75 g, 100 mmol), and the resulting mixture was stirred at 25° C. for 20 h. To the reaction mixture then was added tert-butyl piperazine-1-carboxylate (18.60 g, 100 mmol), and the resulting mixture was stirred at 25° C. for another 24 h. The mixture was diluted with diethyl ether, washed with water (×3) and brine, dried over anhyd. sodium sulfate, filtered, and concentrated. Column chromatography on silica gel (elution: 0-20% diethyl ether/methylene chloride) to afford tert-butyl 4-(pyridin-2-ylcarbamothioyl)piperazine-1-carboxylate (13.60 g) as a colorless solid, following crystallization from a mixture of 1-chlorobutane/hexane; 1H NMR (300 MHz, CDCl3) δ 7.97 (m, 1H), 7.64 (m, 2H), 6.88 (m, 1H), 4.00 (m, 4H), 3.51 (m, 4H), 1.44 (s, 9H).

Provenance & Evidence