9-Benzyl-9H-purine → 9-Benzyl-8-bromo-9H-purine

HRID 1297154Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1297154
[CH2:1]([N:8]1[CH:16]=[N:15][C:14]2[C:9]1=[N:10][CH:11]=[N:12][CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:17]NC(=O)CCC(N)=O>C(Cl)(Cl)Cl>[CH2:1]([N:8]1[C:16]([Br:17])=[N:15][C:14]2[C:9]1=[N:10][CH:11]=[N:12][CH:13]=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 2347019-Benzyl-9H-purineHCID 9834204N-Bromosuccinamide

Produkt 1

HCID 589145899-Benzyl-8-bromo-9H-purine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To a stirred solution of 12 (10.68 g, 50.7 mmol) in chloroform (500 mL) was added N-bromosuccinamide (45.20 g, 253.9 mmol) and the reaction mixture stirred under an atmosphere of nitrogen and at reflux temperature for 5 h. The reaction mixture was transferred to a separatory funnel and washed with saturated sodium sulfite solution (2×250 mL) followed by brine solution (2×250 mL). The chloroform fraction was dried over anhydrous sodium sulfate and concentrated and the reddish oil was purified by flash chromatography on silica gel using EtOAc/hexane (4:6) for elution. Yield 6.05 g. (41.2%). Mp 119-121° C.; 1H NMR (CDCl3): δ 5.53 (s, 2H, CH2), 7.35-7.39 (m, 5H, Ar—H), 9.03 (s, 1H, purine C8—H), 9.09 (s, 1H, purine C2—H).

Aufarbeitung

  1. temperatureat reflux temperature for 5 h
  2. customThe reaction mixture was transferred to a separatory funnel
  3. washwashed with saturated sodium sulfite solution (2×250 mL)
  4. dry with materialThe chloroform fraction was dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customthe reddish oil was purified by flash chromatography on silica gel
  7. washfor elution

Quellen und Nachweise

ORD-Eintrag
ord-dd57689fbb8343d591ef0c3e6323f6e5
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07250421B2

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