Reaktion #304021

Reaktionsgleichung

6-bromopurine

(5-chloro-3-(2-chlorophenyl)quinoxalin-2-yl)methanamine

N,N-diisopropylethylamine

1-butanol

→

N-((5-chloro-3-(2-chlorophenyl)quinoxalin-2-yl)methyl)-9H-purin-6-amine

Lösungsmittel

CH2Cl2 Hexane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe mixture was removed from the
2. 2
   Temperaturheat
3. 3
   Einengenconcentrated under reduced pressure
4. 4
   SonstigeThe residue was purified by flash column chromatography on a silica gel column
5. 5
   Sonstigeto give a light-yellow solid
6. 6
   Filtrationfiltered

Vorschrift

A mixture of 6-bromopurine (0.4553 g, 2.288 mmol), (5-chloro-3-(2-chlorophenyl)quinoxalin-2-yl)methanamine (0.6959 g, 2.288 mmol), and N,N-diisopropylethylamine (0.7970 mL, 4.576 mmol) in 1-butanol (13.46 mL, 2.288 mmol) was stirred at 100° C. After 3.5 h, the mixture was removed from the heat and concentrated under reduced pressure. The residue was purified by flash column chromatography on a silica gel column using 50% of CH2Cl2:MeOH:NH4OH (89:9:1) in CH2Cl2 as eluent to give a light-yellow solid. The light-yellow solid was suspended in CH2Cl2-Hexane (1:1) and filtered to give N-((5-chloro-3-(2-chlorophenyl)quinoxalin-2-yl)methyl)-9H-purin-6-amine as a light-yellow solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 12.93 (1H, s), 8.02-8.16 (4H, m), 7.95 (1H, br. s.), 7.83-7.90 (1H, m), 7.61-7.72 (2H, m), 7.53-7.59 (1H, m), 7.47-7.53 (1H, m), 4.72-4.98 (2H, m), 89676-20-1-1H-NMR; LC-MS (ESI) m/z 422.0 and 424.0 [M+H]+.

Quelle