N-bromobutanimide → 5-Bromo-7-(2-C-methyl-b-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

HRID 2252673Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2252673
[NH2:1][C:2]1[C:3]2[CH:10]=[CH:9][N:8]([C@@H:11]3[O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@@:12]3([CH3:20])[OH:13])[C:4]=2[N:5]=[CH:6][N:7]=1.[Br:21]N1C(=O)CCC1=O>CN(C=O)C>[NH2:1][C:2]1[C:3]2[C:10]([Br:21])=[CH:9][N:8]([C@@H:11]3[O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@@:12]3([CH3:20])[OH:13])[C:4]=2[N:5]=[CH:6][N:7]=1

Komponenten

4

Edukt 2

HCID 67184N-bromobutanimideHCID 30118937-Deaza-2'-C-methyladenosine

Produkt 1

HCID 30118995-Bromo-7-(2-C-methyl-b-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amineAusbeute 36,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a pre-cooled solution (0° C.) of the compound from Step F of Example 2 (28 mg, 0.10 mmol) in DMF (0.5 mL) was added N-bromosuccinimide (0.018 g, 0.10 mmol) in DMF (0.5 mL) dropwise. The solution was stirred at 0° C. for 20 min, then at room temperature for 10 min. The reaction was quenched by addition of methanol (4 mL) and evaporated in vacuo. The crude product was purified on silica gel using methanol/dichloromethane (1:9) as eluent. Fractions containing the product were pooled and evaporated in vacuo to give the desired product (13.0 mg) as a colorless solid.

Aufarbeitung

  1. waitat room temperature for 10 min
  2. customThe reaction was quenched by addition of methanol (4 mL)
  3. customevaporated in vacuo
  4. customThe crude product was purified on silica gel
  5. additionFractions containing the product
  6. customevaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-6a4f1edc340d4fd39fd7725eb7239b93
Quelldatensatz
uspto-grants-2008_01
Patentnummer
US07323453B2

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