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Sodium hydride → (R)-1-(5-acetoxyhexyl)-3-(2-furylmethyl)-7-methylxanthine

HRID 1835707
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1835707
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][N:7]1[C:15]2[N:14]=[CH:13][N:12]([CH3:16])[C:11]=2[C:10](=[O:17])[NH:9][C:8]1=[O:18].[H-].[Na+].[C:21]([O:24][C@H:25]([CH3:31])[CH2:26][CH2:27][CH2:28][CH2:29]I)(=[O:23])[CH3:22]>CS(C)=O>[C:21]([O:24][C@H:25]([CH3:31])[CH2:26][CH2:27][CH2:28][CH2:29][N:9]1[C:10](=[O:17])[C:11]2[N:12]([CH3:16])[CH:13]=[N:14][C:15]=2[N:7]([CH2:6][C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)[C:8]1=[O:18])(=[O:23])[CH3:22]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 224991273-(2-Furylmethyl)-7-methylxanthineHCID 54009360(R)-5-acetoxy-1-iodohexane

Produkt 1

HCID 54209961(R)-1-(5-acetoxyhexyl)-3-(2-furylmethyl)-7-methylxanthineAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

To a stirring suspension 3-(2-furylmethyl)-7-methylxanthine (0.40 g, 1.62 mmol) in dimethylsulfoxide (20 ml) was added sodium hydride (41 mg, 1.71 mmol) in one portion. After stirring for 25 minutes, (R)-5-acetoxy-1-iodohexane (0.46 g, 1.71 mol) was added neat. After stirring at room temperature for 72 hours, the reaction was quenched by the addition of water (75 ml) and extracted with ethyl acetate (3×35 ml). The combined extracts were washed with saturated aqueous sodium chloride solution (2×35 ml), dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with ethyl acetate to give (R)-1-(5-acetoxyhexyl)-3-(2-furylmethyl)-7-methylxanthine (0.49 g, 78% yield) as a colorless oil.

Aufarbeitung

  1. stirringAfter stirring at room temperature for 72 hours
  2. customthe reaction was quenched by the addition of water (75 ml)
  3. extractionextracted with ethyl acetate (3×35 ml)
  4. washThe combined extracts were washed with saturated aqueous sodium chloride solution (2×35 ml)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography on silica gel eluting with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-5f1e9170d59f41fe81d1a9109cadb681
Quelldatensatz
uspto-grants-2004_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06774130B2

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