N-Iodosuccinimide → 6-Chloro-7-iodo-7-deazapurine

HRID 10160

Reaktionsgleichung

Reaktionsgleichung von HRID 10160
[CH:1]1[C:5]2[C:6]([Cl:10])=[N:7][CH:8]=[N:9][C:4]=2[NH:3][CH:2]=1.[I:11]N1C(=O)CCC1=O>CN(C=O)C>[CH:2]1[NH:3][C:4]2[N:9]=[CH:8][N:7]=[C:6]([Cl:10])[C:5]=2[C:1]=1[I:11]

Komponenten

4

Edukt 2

HCID 120273N-IodosuccinimideHCID 53566827H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-

Produkt 1

HCID 148092816-Chloro-7-iodo-7-deazapurineAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

6-Chloro-7-deazapurine 10.75 g (70 mmol) and N-iodosuccinimide (16.8 g, 75 mmol) were dissolved in 400 ml of dry DMF and left at ambient temperature in the darkness over night. The solvent was evaporated. The dark residue was distributed between 500 ml of ethyl acetate and 150 ml of 10% Na2SO3. Organic fraction was washed with 10% Na2SO3 (2×100 ml), brine (150 ml), dried over Na2SO4 and evaporated. The yellow residue was crystallized from ethanol to yield 16.2 g (83%) of the title compound as off white crystals. The mother liquid was evaporated, dissolved in toluene, and purified by flush chromatography on silica gel (7×4 cm). The column was washed with toluene until the eluent was colorless than the title compound was eluted with 5% ethyl acetate in toluene to give additional 3.5 g of the title product.

Aufarbeitung

  1. waitleft at ambient temperature in the darkness over night
  2. customThe solvent was evaporated
  3. washOrganic fraction was washed with 10% Na2SO3 (2×100 ml), brine (150 ml)
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe yellow residue was crystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-080e4b8602244c829a89bdfa381e91f1
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07094768B2

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