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

HRID 1836245Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1836245
[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 62 (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 rt 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 rt 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-044a27a311e045a481805db58816c2d4
Quelldatensatz
uspto-grants-2004_08
Patentnummer
US06777395B2

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