Thionyl Chloride → Ethyl 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylate

HRID 1011298

Reaktionsgleichung

Reaktionsgleichung von HRID 1011298
[CH2:1]([O:3][C:4]([C:6]1[NH:15][C:9]2[N:10]=[CH:11][N:12]=[C:13](O)[C:8]=2[CH:7]=1)=[O:5])[CH3:2].S(Cl)([Cl:18])=O.C([O-])(O)=O.[Na+]>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[NH:15][C:9]2[N:10]=[CH:11][N:12]=[C:13]([Cl:18])[C:8]=2[CH:7]=1)=[O:5])[CH3:2]

Komponenten

5

Edukt 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 178468549HCID 178468549, Verbindung

Produkt 1

HCID 21262606Ethyl 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a round bottom flask equipped with a magnetic stir bar was added 4-hydroxy-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid ethyl ester (0.300 g, 1.3 mmol, 1.0 eq.), thionyl chloride (5 ml), and DMF (1 ml). The mixture was refluxed for 4 hour at which time the reaction was poured onto ice and NaHCO3. The aqueous layer was then extracted with ethyl acetate (2×). The organic layer was washed with water and brine, dried (Na2SO4), and concentrated in vacuo to give 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid ethyl ester as a brown solid (0.35 g 100% yield). MS (ESI, negative) for C9H8ClN3O2: 224 (M-H).

Aufarbeitung

  1. customTo a round bottom flask equipped with a magnetic stir bar
  2. temperatureThe mixture was refluxed for 4 hour at which time the reaction
  3. extractionThe aqueous layer was then extracted with ethyl acetate (2×)
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-3199c3446e374227b9bec45255bb01c9
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07977345B2

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