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

HRID 2369237Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2369237
[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)adenineAusbeute 97,9 %

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 (EtOAc:CH2Cl2:MeOH at 2:2:1) to provide the product (1.29 g, 97%). 1H NMR (400 MHz, acetone-d6) 8.07 (s, 1H), 7.28 (s, 1H), 7.15 (s, 1H), 7.08 (bs, 2H), 6.13 (s, 2H); MS m/z 366.0 (M+H)+.

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 (EtOAc:CH2Cl2:MeOH at 2:2:1)

Quellen und Nachweise

ORD-Eintrag
ord-36f7b41463c7459691c41bee2eaab5eb
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08703942B2

Notizen zur Reaktion

Wird geladen…