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

HRID 216839

Reaktionsgleichung

Br[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[NH:4][CH:5]=[N:6]2.[Cl:11][C:12]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:13]=1[N:14]=[C:15]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[Cl:30])[C:16]([CH2:22][NH2:23])=[N:17]2.C(N(CC)C(C)C)(C)C.C(O)CCC>C(Cl)Cl.CCCCCC>[Cl:11][C:12]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:13]=1[N:14]=[C:15]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[Cl:30])[C:16]([CH2:22][NH:23][C:2]1[N:10]=[CH:9][N:8]=[C:7]3[C:3]=1[N:4]=[CH:5][NH:6]3)=[N:17]2

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

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]+.

Aufarbeitung

customthe mixture was removed from the
temperatureheat
concentrationconcentrated under reduced pressure
customThe residue was purified by flash column chromatography on a silica gel column
customto give a light-yellow solid
filtrationfiltered

Quellen und Nachweise

ORD-Eintrag: ord-19f21b9fc8274225bfeb4732a8d0b1d8
Quelldatensatz: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08193199B2

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