Potassium hydroxy sulfite → 2-Chloro-7-(pentan-3-yl)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid

HRID 2189314Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2189314
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[CH:10]=[C:9]([CH:11]=[O:12])[N:8]([CH:13]([CH2:16][CH3:17])[CH2:14][CH3:15])[C:6]=2[N:7]=1.[OH:18]OS([O-])=O.[K+]>CN(C=O)C>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[CH:10]=[C:9]([C:11]([OH:18])=[O:12])[N:8]([CH:13]([CH2:16][CH3:17])[CH2:14][CH3:15])[C:6]=2[N:7]=1

Komponenten

4

Edukt 2

HCID 23707502Potassium hydroxy sulfiteHCID 735546542-Chloro-7-(pentan-3-yl)-7H-pyrrolo[2,3-d]pyrimidine-6-carbaldehyde

Produkt 1

HCID 735546592-Chloro-7-(pentan-3-yl)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acidAusbeute 43,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of 2-chloro-7-(1-ethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-6-carbaldehyde (283 mg, 1.11 mmol) in DMF (3 mL) is added oxone (820 mg, 1.33 mmol) at room temperature. The mixture is stirred at room temperature for 5 h and is quenched with 20% Na2S2O3 aqueous solution. After stirring for 10 min, the reaction mixture is acidified with 1N HCl aqueous solution (pH=5). The mixture is extracted with dichloromethane, dried over Na2SO4 and concentrated in vacuo. The solid is filtered, washed with acetonitrile, and dried under vacuum to give 130 mg of 2-chloro-7-(1-ethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid as a pale brown solid.

Aufarbeitung

  1. customis quenched with 20% Na2S2O3 aqueous solution
  2. stirringAfter stirring for 10 min
  3. extractionThe mixture is extracted with dichloromethane
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. filtrationThe solid is filtered
  7. washwashed with acetonitrile
  8. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-6030276e7895451bb622049753c39402
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08324225B2

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