Sodium Hydroxide → 4-chloro-6-(1-naphthyl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 1678015Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1678015
[Cl:1][C:2]1[C:3]2[CH:10]=[C:9]([C:11]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH:14]=[CH:13][CH:12]=3)[N:8](S(C3C=CC=CC=3)(=O)=O)[C:4]=2[N:5]=[CH:6][N:7]=1.[OH-].[Na+]>C1COCC1.CO>[Cl:1][C:2]1[C:3]2[CH:10]=[C:9]([C:11]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH:14]=[CH:13][CH:12]=3)[NH:8][C:4]=2[N:5]=[CH:6][N:7]=1

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 866187344-chloro-6-(1-naphthyl)-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine

Produkt 1

HCID 866187354-chloro-6-(1-naphthyl)-7H-pyrrolo[2,3-d]pyrimidineAusbeute 69,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 4-chloro-6-(1-naphthyl)-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidine (350 mg, 0.73 mmol) in THF (2.50 mL) was added a solution of NaOH (205 mg, 5.13 mmol) in methanol (1.19 mL), and the mixture was stirred for 15 minutes. After quenching by addition of saturated NH4Cl solution (80.0 mL), the mixture was extracted with ethyl acetate (3×100 mL). The organic layers were combined, dried over MgSO4, filtered, and evaporated under vacuum. The residue was dissolved in a small amount of methanol, and the suspension was filtered through a glass pad filter. The white solid was dried under high to afford the title compound (141 mg, 65%).

Aufarbeitung

  1. customAfter quenching by addition of saturated NH4Cl solution (80.0 mL)
  2. extractionthe mixture was extracted with ethyl acetate (3×100 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated under vacuum
  6. dissolutionThe residue was dissolved in a small amount of methanol
  7. filtrationthe suspension was filtered through a glass pad
  8. filtrationfilter
  9. customThe white solid was dried under high

Quellen und Nachweise

ORD-Eintrag
ord-3b49f802fbc14f5f82db9b36254908cb
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08008307B2

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