5-Bromo-6-iodobenzo[d][1,3]dioxole → 8-(6-Bromo-benzo[1,3]dioxol-5-ylsulfanyl)adenine

HRID 1173527Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1173527
[SH:1][C:2]1[NH:10][C:9]2[C:4](=[N:5][CH:6]=[N:7][C:8]=2[NH2:11])[N:3]=1.CC1C=CC2C=CC3C=CC(C)=NC=3C=2N=1.O.O(C(C)(C)C)[Na].[Br:35][C:36]1[C:44](I)=[CH:43][C:39]2[O:40][CH2:41][O:42][C:38]=2[CH:37]=1>[Cu]I.CN(C=O)C>[Br:35][C:36]1[C:44]([S:1][C:2]2[NH:10][C:9]3[C:4](=[N:5][CH:6]=[N:7][C:8]=3[NH2:11])[N:3]=2)=[CH:43][C:39]2[O:40][CH2:41][O:42][C:38]=2[CH:37]=1

Komponenten

7

Edukt 4

HCID 35498645-Bromo-6-iodobenzo[d][1,3]dioxoleHCID 162112342,9-Dimethyl-1,10-phenanthroline hydrateHCID 178418730sodium 2-methylpropan-2-olateHCID 178508691HCID 178508691, Verbindung

Produkt 1

HCID 114740228-(6-Bromo-benzo[1,3]dioxol-5-ylsulfanyl)adenine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

8-Mercaptoadenine (602 mg, 3.6 mmol), neocuproine hydrate (81 mg, 0.36 mmol), CuI (69 mg, 0.36 mmol), NaO-t-Bu (692 mg, 7.2 mmol), 5-bromo-6-iodo-benzo[1,3]dioxole (3.53 g, 10.8 mmol) and anhydrous DMF (24 mL) were charged in a nitrogen box. The vessel was sealed with Teflon tape, placed in an oil bath (110° C.) and magnetically stirred for 24 h. The solvent was removed under high vacuum and the crude purified by column chromatography on silica gel

Aufarbeitung

  1. customplaced in an oil bath
  2. customThe solvent was removed under high vacuum
  3. customthe crude purified by column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-6bbd4e19302a4a309c7d972bf8e42a9d
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07834181B2

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