Cyclopropylamine → HCID 86725119, compound

Participants

Reaction Steps

2-Chloropyrimidine-4-carboxylic acid (0.516 g, 3.25 mmol) (Maybridge Chemicals, Maybridge, UK), DIPEA (0.94 mL, 5.42 mmol) and PyBop (1.69 g, 3.25 mmol) were weighed into a 150 mL RBF and dissolved in dioxane (15 mL). The solution was stirred at RT, then cooled to 0° C., and stirred for 5 min. Cyclopropylamine (0.38 mL, 5.42 mmol) was added, and the solution was stirred at 0° C. for 1 h. The mixture became solid. Additional dioxane was added (6 mL), the flask was removed from the ice bath and the contents were stirred at RT for 68 h. EtOAc was added and the mixture was washed with water (75 mL), 1 N NaOH (75 mL) and brine (75 mL). The crude material was purified by flash chromatography using an ISCO Combiflash Rf(25 g Thomson Single Step silica gel column; 20-100% EtOAc in hexanes) to afford 2-chloro-N-cyclopropylpyrimidine-4-carboxamide (0.139 g, 0.703 mmol, 25.9% yield) as a yellow oil. MS (ESI, pos. ion) m/z: 197.9 (M+H)+.

Provenance & Evidence