Reaktion #329101

ord-356a28e8e87943438bf9db47ad58cdd4

Reaktionsgleichung

COc1cc2nc(CCl)n(-c3ccccc3Cl)c(=O)c2cc1OC
Intermediate 2a
COc1cc2nc(CCl)n(-c3ccccc3Cl)c(=O)c2cc1OC
2-Chloromethyl-3-(2-chlorophenyl)-6,7-dimethoxy-3H-quinazolin-4-one
Nc1ncnc2nc[nH]c12
adenine
O=C([O-])[O-].[K+].[K+]
K2CO3
COc1cc2nc(Cn3cnc4c(N)ncnc43)n(-c3ccccc3Cl)c(=O)c2cc1OC
beige solid
Ausbeute 65.0%
COc1cc2nc(Cn3cnc4c(N)ncnc43)n(-c3ccccc3Cl)c(=O)c2cc1OC
2-(6-Aminopurin-9-ylmethyl)-3-(2-chlorophenyl)-6,7-dimethoxy-3H-quinazolin-4-one
Ausbeute 65.0%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigePrepared
  2. 2
    SonstigeThe crude product was recrystallized from ethanol (EtOH)

Vorschrift

Prepared according to Procedure C using Intermediate 2a (200 mg, 0.546 mmol), adenine (81 mg, 0.601 mmol), K2CO3 (83 mg, 0.601 mmol), and DMF (4 mL). The crude product was recrystallized from ethanol (EtOH) to provide 164 mg of a beige solid (65%), mp 281.5-282.7° C. (decomposes). 1H NMR (DMSO-d6) δ: 8.06 (s, 1H); 8.04 (s, 1H); 7.76-7.81 (m, 1H); 7.70-7.76 (m, 1H); 7.60-7.67 (m, 2H); 7.45 (s, 1H); 7.22 (s, 2H); 6.90 (s, 1H); 5.08 (d, J=17 Hz, 1H); 4.91 (d, J=17 Hz, 1H); 3.87 (s, 3H); 3.87 (s, 3H). 13C NMR (DMSO-d6) ppm: 159.9, 156.2, 155.4, 152.9, 150.0, 149.7, 149.4, 143.0, 141.9, 133.7, 132.1, 131.9, 131.2, 130.8, 129.3, 118.4, 113.6, 108.4, 105.8, 56.5, 56.1, 44.7. MS (ES): m/z 464.1 (M+). Anal. calcd. for C22H18ClN7O3∘0.1C2H6O∘0.05KCl: C, 56.47; H, 3.97; Cl, 7.88; N, 20.76. Found: C, 56.54; H, 4.05; Cl, 7.77; N, 20.55.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08653077B2uspto-grants-2014_02