Reaktion #329102

ord-9c0b3e0db9794f86be9d023ebc14ab4d

Reaktionsgleichung

O=c1c2cc(Cl)ccc2nc(CCl)n1-c1ccccc1Cl
Intermediate 2d
O=c1c2cc(Cl)ccc2nc(CCl)n1-c1ccccc1Cl
6-Chloro-2-chloromethyl-3-(2-chlorophenyl)-3H-quinazolin-4-one
Nc1ncnc2nc[nH]c12
adenine
O=C([O-])[O-].[K+].[K+]
K2CO3
Nc1ncnc2c1ncn2Cc1nc2ccc(Cl)cc2c(=O)n1-c1ccccc1Cl
yellow solid
Ausbeute 39.0%
Nc1ncnc2c1ncn2Cc1nc2ccc(Cl)cc2c(=O)n1-c1ccccc1Cl
2-(6-Aminopurin-9-ylmethyl)-6-chloro-3-(2-chlorophenyl)-3H-quinazolin-4-one
Ausbeute 39.0%

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 2d (100 mg, 0.294 mmol), adenine (44 mg, 0.323 mmol), K2CO3 (45 mg, 0.323 mmol), and DMF (1 mL). The crude product was recrystallized from EtOH to provide 50 mg of a yellow solid (39%), mp 294.5-294.8° C. (decomposes). 1H NMR (DMSO-d6) δ: 8.10 (d, J=2.2 Hz, 1H); 8.05 (s, 1H); 8.03 (s, 1H); 7.86 (dd, J=2.4, 8.8 Hz, 1H); 7.75-7.82 (m, 2H); 7.59-7.67 (m, 2H); 7.53 (d, J=8.7 Hz, 1H); 7.22 (br s, 2H); 5.13 (d, J=17 Hz, 1H); 4.95 (d, J=17 Hz, 1H). 13C NMR (DMSO-d6) ppm: 159.7, 156.2, 152.9, 151.9, 150.1, 145.5, 141.8, 135.7, 133.1, 132.3, 132.2, 131.9, 131.1, 130.9, 130.0, 129.4, 125.9, 122.0, 118.4, 44.9. MS (ES): m/z 438.0 (M+). Anal. calcd. for C20H13Cl2N7O: C, 54.81; H, 2.99; N, 22.37. Found: C, 54.72; H, 2.87; N, 22.18.

Quelle

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