Pyridine → HCID 70146783, Verbindung

HRID 611462

Reaktionsgleichung

Reaktionsgleichung von HRID 611462
[OH2:1].[C@@H:2]1([N:10]2[C:19]3[N:18]=[CH:17][N:16]=[C:14]([NH2:15])[C:13]=3[N:12]=[CH:11]2)[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[CH2:3]1.N1C=CC=CC=1.[H-].[Na+].[N+:28]([C:31]1[CH:38]=[CH:37][CH:36]=[CH:35][C:32]=1[CH2:33]Br)([O-:30])=[O:29]>CN(C=O)C>[N+:28]([C:31]1[CH:38]=[CH:37][CH:36]=[CH:35][C:32]=1[CH2:33][C@@:2]1([N:10]2[C:19]3[N:18]=[CH:17][N:16]=[C:14]([NH2:15])[C:13]=3[N:12]=[CH:11]2)[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[C@H:3]1[OH:1])([O-:30])=[O:29]

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 24758Sodium hydrideHCID 77569alpha-Bromo-2-nitrotolueneHCID 95491722'-Deoxyadenosine monohydrate

Produkt 1

HCID 70146783HCID 70146783, VerbindungAusbeute 39,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2'-Deoxyadenosine monohydrate (538 mg, 2.0 mmol, Aldrich Chemical, Milwaukee, Wisc.) was dried by evaporation with anhydrous pyridine (2 times, 10 ml) under vacuum. The residue was dissolved in anhydrous DMF (10 ml, Aldrich, Milwaukee, Wisc.) under an argon atmosphere, and sodium hydride (88 mg, 2.2 mmol, 1.1 equiv, 60% dispersion in oil) was added and stirred for 40 mins at room temperature. 2-Nitrobenzyl bromide (710 mg, 3.3 mmol, 1.5 equiv) was added and the solution was stirred for 4 hours at room temperature. The DMF was removed by evaporation under vacuum, and the residue was partitioned between ethyl acetate and water (20 ml each). The aqueous phase was extracted with ethyl acetate (20 ml) and the combined extracts were washed with water (20 ml) and dried over magnesium sulfate, filtered and evaporated. The crude product was purified by column chromatography on silica gel (50 g, using 3% MeOH in CH2Cl2) to yield 2'-deoxy-N6 -bis-ortho-nitrobenzyladenosine (320 mg, 30%).

Aufarbeitung

  1. stirringthe solution was stirred for 4 hours at room temperature
  2. customThe DMF was removed by evaporation under vacuum
  3. customthe residue was partitioned between ethyl acetate and water (20 ml each)
  4. extractionThe aqueous phase was extracted with ethyl acetate (20 ml)
  5. washthe combined extracts were washed with water (20 ml)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude product was purified by column chromatography on silica gel (50 g, using 3% MeOH in CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-3c2e13034cc941bc92ba7f9e3993e05c
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US06001611

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