Reaktion #329104

ord-7f915e2b0eff484c85415975aeb4daa6

Reaktionsgleichung

Cc1cccc2nc(CCl)n(-c3ccccc3Cl)c(=O)c12
Intermediate 2g
Cc1cccc2nc(CCl)n(-c3ccccc3Cl)c(=O)c12
2-Chloromethyl-3-(2-chlorophenyl)-5-methyl-3H-quinazolin-4-one
Nc1ncnc2nc[nH]c12
adenine
O=C([O-])[O-].[K+].[K+]
K2CO3
Cc1cccc2nc(Cn3cnc4c(N)ncnc43)n(-c3ccccc3Cl)c(=O)c12
pale yellow solid
Ausbeute 28.4%
Cc1cccc2nc(Cn3cnc4c(N)ncnc43)n(-c3ccccc3Cl)c(=O)c12
2-(6-Aminopurin-9-ylmethyl)-3-(2-chlorophenyl)-5-methyl-3H-quinazolin-4-one
Ausbeute 28.4%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigePrepared
  2. 2
    SonstigeThe crude product was recrystallized from EtOH

Vorschrift

Prepared according to Procedure C using Intermediate 2g (250 mg, 0.783 mmol), adenine (116 mg, 0.862 mmol), K2CO3 (119 mg, 0.862 mmol), and DMF (4 mL). The crude product was recrystallized from EtOH to provide 93 mg of a pale yellow solid (28%), mp 190.7-190.9° C. 1H NMR (DMSO-d6) δ: 8.05 (s, 1H); 8.03 (s, 1H); 7.76-7.79 (m, 1H); 7.71-7.74 (m, 1H); 7.59-7.67 (m, 1H); 7.34 (d, J=7.4 Hz, 1H); 7.28 (d, J=8.2 Hz, 1H); 7.24 (br s, 2H); 5.07 (d, J=17 Hz, 1H); 4.92 (d, J=17 Hz, 1H); 2.73 (s, 3H). 13C NMR (DMSO-d6) ppm: 161.1, 156.2, 152.8, 150.9, 150.1, 148.3, 141.9, 141.0, 134.6, 133.6, 132.2, 131.9, 131.3, 130.8, 130.3, 129.3, 125.9, 119.1, 118.4, 44.8, 22.8. MS (ES): m/z 418.1 (M+). Anal. calcd. for C2H16ClN7O.H2O: C, 57.87; H, 4.16; Cl, 8.13; N, 22.49. Found: C, 57.78; H, 3.99; Cl, 8.38; N, 22.32.

Quelle

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