Reaktion #78369

ord-ef05ffb40df34eb2a3d154b30737afc3

Reaktionsgleichung

Cl
hydrochloric acid
Nc1nc(Cl)c2[nH]cnc2n1
2-amino-6-chloropurine
O=C([O-])[O-].[K+].[K+]
potassium carbonate
O=C(O)CBr
bromoacetic acid
Nc1nc(Cl)c2ncn(CC(=O)O)c2n1
2-Amino-6-chloro-9-carboxymethylpurine

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Filtrationthe solution was filtered through Celite
  2. 2
    Sonstigeto give a clear yellow solution
  3. 3
    FiltrationThe precipitate was filtered
  4. 4
    Sonstigedried, in vacuo
  5. 5
    SonstigeYield (3.02 g; 44.8%)

Vorschrift

To a suspension of 2-amino-6-chloropurine (5.02 g; 29.6 mmol) and potassium carbonate (12.91 g; 93.5 mmol) in DMF (50 ml) was added bromoacetic acid (4.70 g; 22.8 mmol). The mixture was stirred vigorously for 20 h. under nitrogen. Water (150 ml) was added and the solution was filtered through Celite to give a clear yellow solution. The solution was acidified to a pH of 3 with 4 N hydrochloric acid. The precipitate was filtered and dried, in vacuo, over sicapent. Yield (3.02 g; 44.8%). 1H-NMR(DMSO-d6): d=4.88 ppm (s,2H); 6.95 (s,2H); 8.10 (s,1H).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06710163B1uspto-grants-2004_03