Methyl iodide → 4-chloro-5-iodo-7-methyl-7H-pyrrolo[2,3-d]pyrimidine

HRID 82254

Reaktionsgleichung

Reaktionsgleichung von HRID 82254
[Cl:1][C:2]1[C:3]2[C:10]([I:11])=[CH:9][NH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[C:12]([O-])([O-])=O.[Cs+].[Cs+].CI>CN(C=O)C>[Cl:1][C:2]1[C:3]2[C:10]([I:11])=[CH:9][N:8]([CH3:12])[C:4]=2[N:5]=[CH:6][N:7]=1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 148092816-Chloro-7-iodo-7-deazapurine

Produkt 1

HCID 426094624-chloro-5-iodo-7-methyl-7H-pyrrolo[2,3-d]pyrimidineAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (Preparation 225, 30 g, 0.1 mol), Cs2CO3 (50 g, 0.15 mol) in DMF (150 mL), MeI (28.4 g, 0.2 mol) was added dropwise at 0° C. After addition, the mixture was stirred at room temperature for 10 hours. The reaction mixture was cooled to 0° C. and quenched by the addition of water (500 mL). Then the solid was collected by filtration and washed with Et2O (100 mL) to afford 4-chloro-5-iodo-7-methyl-7H-pyrrolo[2,3-d]pyrimidine as a brown solid in 61% yield, 20 g.

Aufarbeitung

  1. additionwas added dropwise at 0° C
  2. additionAfter addition
  3. temperatureThe reaction mixture was cooled to 0° C.
  4. customquenched by the addition of water (500 mL)
  5. filtrationThen the solid was collected by filtration
  6. washwashed with Et2O (100 mL)

Quellen und Nachweise

ORD-Eintrag
ord-5183687992584b168accd678f781f565
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846698B2

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