Acetone → HCID 86635891, compound

Participants

Reaction Conditions

Reaction Steps

In a round bottom flask, ethyl 3-(cyclohexylamino)-2,2-difluoropropanoate (11.05 g, 50 mmol) was dissolved in acetone (100 mL), and added K2CO3 (13.8 g, 100 mmol) to it. Cooled the round bottom flask to 0° C. in an ice bath. After 20 min, added 2,4-dichloro 5-nitropyrimidine (9.70 g, 50 mmol) in acetone (25 mL) dropwise and continued stirring for another 30 min at 0° C., then allowed to warm up to room temperature, continued for 12 hrs. Then evaporated the acetone washed with water and extracted into EtOAc (300 mL) dried over Na2SO4 and evaporated. The crude gummy solid was purified on Combiflash (ISCO) using hexane-EtOAc as solvent system to obtain the desired compound (11.85 g, 60%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.02-1.31 (m, 3 H) 1.42-1.68 (m, 3 H) 1.75 (d, J=9.09 Hz, 4 H) 3.33 (m, 1 H) 3.80 (s, 3 H) 4.40 (t, J=14.02 Hz, 2 H) 8.92 (s, 1 H). MS (ES) [M+H] calculated for C15H19ClF2N4O4, 393; found 393.

Provenance & Evidence