Iodoethane → 3-Benzyloxy-1-ethyl-5,6,8-trifluoro-7-pyrrolidin-1-yl-1H-quinazoline-2,4-dione

HRID 2270245Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2270245
[CH2:1]([O:8][N:9]1[C:18](=[O:19])[C:17]2[C:12](=[C:13]([F:23])[C:14](F)=[C:15]([F:21])[C:16]=2[F:20])[NH:11][C:10]1=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1.[CH2:30](I)[CH3:31].[H-].[Na+]>CC(N(C)C)=O.CN(C=O)C>[CH2:1]([O:8][N:9]1[C:18](=[O:19])[C:17]2[C:12](=[C:13]([F:23])[C:14]([N:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)=[C:15]([F:21])[C:16]=2[F:20])[N:11]([CH2:30][CH3:31])[C:10]1=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 31268PyrrolidineHCID 226328803-Benzyloxy-5,6,7,8-tetrafluoro-1H-quinazoline-2,4-dione

Produkt 1

HCID 226329973-Benzyloxy-1-ethyl-5,6,8-trifluoro-7-pyrrolidin-1-yl-1H-quinazoline-2,4-dioneAusbeute 22,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A solution of 3-benzyloxy-5,6,7,8-tetrafluoro-1H-quinazoline-2,4-dione (Example W-3, 0.90 g, 2.7 mmol), in DMA (10 mL) was reacted with pyrrolidine (0.55 mL, 6.6 mmol) and heated to 60° C. for 3 hours. The mixture was then cooled and quenched with H2O and acidified with citric acid. The mixture was then extracted with ethyl acetate, dried with MgSO4, and concentrated. The residue was triturated with diethyl ether/hexanes and the solid filtered and dried (0.87 g). A portion of the solid (0.500 g, 1.28 mmol) was dissolved in DMF and reacted with ethyl iodide (1.0 mL, 12.77 mmol) and sodium hydride (0.060 g, 1.5 mmol). The mixture was stirred for 16 hours. The mixture was quenched with H2O and extracted with ethyl acetate. The organic layers were combined, dried with sodium sulfate, and concentrated. The residue was triturated with diethyl ether and filtered to yield 0.25 g of the title compound as a solid.

Aufarbeitung

  1. temperatureThe mixture was then cooled
  2. customquenched with H2O
  3. extractionThe mixture was then extracted with ethyl acetate
  4. dry with materialdried with MgSO4
  5. concentrationconcentrated
  6. customThe residue was triturated with diethyl ether/hexanes
  7. filtrationthe solid filtered
  8. customdried (0.87 g)
  9. customThe mixture was quenched with H2O
  10. extractionextracted with ethyl acetate
  11. dry with materialdried with sodium sulfate
  12. concentrationconcentrated
  13. customThe residue was triturated with diethyl ether
  14. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-bbe7ccc635db47c6bea040d0e8ed53ce
Quelldatensatz
uspto-grants-2001_12
Patentnummer
US06331538B1

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