Tert-Butyl nitrite → 9-Benzyl-9H-purine

HRID 1297153

Reaktionsgleichung

Reaktionsgleichung von HRID 1297153
[CH2:1]([N:8]1[CH:16]=[N:15][C:14]2[C:9]1=[N:10][CH:11]=[N:12][C:13]=2N)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N(OC(C)(C)C)=O>C1COCC1.C(Cl)(Cl)Cl>[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:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 10906Tert-Butyl nitriteHCID 202629-(Phenylmethyl)-9H-purin-6-amine

Produkt 1

HCID 2347019-Benzyl-9H-purine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
62.5 °C

Versuchsvorschrift

To a stirred suspension of 9-benzyladenine (6) (22.0 g, 97.6 mmol) in anhydrous THF (500 mL) was added t-butyl nitrite (9.34 g, 478.5 mmol) and the reaction mixture heated under an atmosphere of nitrogen at 60-65° C. for 4 h. THF and the excess reagent were distilled off and the residue obtained redissolved in chloroform (100 mL) and washed with brine solution (2×50 mL). The chloroform layer was dried over anhydrous sodium sulfate and distilled off to give a reddish oil, which was purified by flash chromatography on silica gel using EtOAc/hexane (8:2) for elution. Yield 10.68 g (42.3%). Mp 99-100° C. 1H NMR (CDCl3): δ 5.49 (s, 2H, CH2), 7.34-7.40 (m, 5H, Ar—H), 8.10 (s, 1H, purine C6—H), 9.06 (s, 1H, purine C8H), 9.20 (s, 1H, purine C2H).

Aufarbeitung

  1. distillationTHF and the excess reagent were distilled off
  2. customthe residue obtained
  3. washwashed with brine solution (2×50 mL)
  4. dry with materialThe chloroform layer was dried over anhydrous sodium sulfate
  5. distillationdistilled off
  6. customto give a reddish oil, which
  7. customwas purified by flash chromatography on silica gel
  8. washfor elution

Quellen und Nachweise

ORD-Eintrag
ord-260b257c25d94c08a3539aa93c66f71e
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07250421B2

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