Cyclopropylamine → HCID 86725119, compound

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)+.

1. temperaturecooled to 0° C.
2. stirringstirred for 5 min
3. stirringthe solution was stirred at 0° C. for 1 h
4. customthe flask was removed from the ice bath
5. stirringthe contents were stirred at RT for 68 h
6. additionEtOAc was added
7. washthe mixture was washed with water (75 mL), 1 N NaOH (75 mL) and brine (75 mL)
8. customThe crude material was purified by flash chromatography

ORD record

ord-43c06c15d36b49f98874cad252f64495

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09321756B2