Methanol → 4-chloro-6-phenyl-7H-pyrrolo[2,3-d]pyrimidine

HRID 988822Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 988822
C1(S([N:10]2[C:14]3[N:15]=[CH:16][N:17]=[C:18]([Cl:19])[C:13]=3[CH:12]=[C:11]2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)(=O)=O)C=CC=CC=1.CO.[OH-].[Na+]>C1COCC1>[Cl:19][C:18]1[C:13]2[CH:12]=[C:11]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[NH:10][C:14]=2[N:15]=[CH:16][N:17]=1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 224845527-Benzenesulfonyl-4-chloro6-phenyl-7H-pyrrolo[2,3-d]pyrimidine

Produkt 1

HCID 224844424-chloro-6-phenyl-7H-pyrrolo[2,3-d]pyrimidineAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The product from Method C was dissolved in 10 mL of THF and to this solution was added 5.0 mL of methanol and 1.0 grams of NaOH. The reaction mixture was stirred for 15 minutes, concentrated in vacuo and partitioned between a saturated aqueous solution of ammonium chloride (NH4Cl) and ethyl acetate. The resulting aqueous layer was extracted twice with ethyl acetate. The ethylacetate layers were combined, washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The crude product was purified by silica-gel chromatography (1:5 ethyl-acetate/hexane) to obtain 0.59 grams (76%) of the title compound as a pale yellow solid, mp 145° C. (dec). LRMS: 230, 232 (M+2).

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. custompartitioned between a saturated aqueous solution of ammonium chloride (NH4Cl) and ethyl acetate
  3. extractionThe resulting aqueous layer was extracted twice with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by silica-gel chromatography (1:5 ethyl-acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-190a62d020ab4fb092b84635bf2cd574
Quelldatensatz
uspto-grants-2003_10
Patentnummer
US06635762B1

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