Ethanol → Dichloromethane methanol ammonium hydroxide

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-chloropurine (0.147 g, 0.954 mmol), (5-chloro-3-(2-(trifluoro-methyl)phenyl)quinoxalin-2-yl)methanamine (0.3223 g, 0.954 mmol), and N,N-diisopropylethylamine (0.332 mL, 1.91 mmol) in ethanol (5.61 mL, 0.954 mmol) was stirred at 75° C. After 19 h, the mixture was removed from the heat and concentrated under reduced pressure. The residue was purified by column chromatography on a 40 g of Redi-Sep™ column using 0 to 100% gradient of EtOAc in hexane over 14 min, then 100% isocratic of EtOAc for 10 min, then 0 to 65% gradient of CH2Cl2:MeOH:NH4OH (89:9:1) in CH2Cl2 over 10 min, then 65% isocratic of CH2Cl2:MeOH:NH4OH (89:9:1) in CH2Cl2 for 10 min, then 65% to 100% gradient of CH2Cl2:MeOH:NH4OH (89:9:1) in CH2Cl2 over 4 min, and then 100% isocratic of CH2Cl2:MeOH:NH4OH (89:9:1) for 4 min as eluent to give the desired product as a brown solid. The brown solid was suspended in CH2Cl2 filtered to give N-((5-chloro-3-(2-(trifluoromethyl)phenyl)quinoxalin-2-yl)methyl)-9H-purin-6-amine as an-off-white solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 12.94 (1H, s), 7.57-8.34 (10H, m), 4.76 (2H, d, J=55.9 Hz); LC-MS (ESI) m/z 456.1 [M+H]+.

Provenance & Evidence