Sodium hydride → HCID 23516881, Verbindung

HRID 1835738Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1835738
[NH2:1][C:2]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6](=[O:15])[NH:5][C:4](=[O:16])[C:3]=1[NH:17][CH3:18].[H-].[Na+].[C:21]([O:24][C@H:25]([CH3:31])[CH2:26][CH2:27][CH2:28][CH2:29]Cl)(=[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:5]1[C:4](=[O:16])[C:3]([NH:17][CH3:18])=[C:2]([NH2:1])[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]1=[O:15])(=[O:23])[CH3:22]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 7262256-AMINO-1-BENZYL-5-METHYLAMINOURACILHCID 110194345-(R)-Acetoxy-1-chlorohexane

Produkt 1

HCID 23516881HCID 23516881, VerbindungAusbeute 47,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

6-Amino-1-benzyl-5-methylaminouracil (11 g, 43 mmol) was added to a suspension of sodium hydride (1.032 mg, 43 mmol) in anhydrous dimethylsulfoxide (75 ml). After stirring for 30 minutes, (R)-5-acetoxy-1-chlorohexane (7.675 g, 43 mmol) was added. The mixture was heated at 70-80° C. for 12 hours. After cooling to room temperature, the reaction was quenched by the addition of water (150 ml) and extracted with ethyl acetate (3×125 ml). The combined extracts were washed with water (2×50 25 ml), with saturated aqueous sodium chloride solution (50 ml), dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel eluting with ethyl acetate to provide (R)-3-(5-acetoxyhexyl)-6-amino-1-benzyl-5-methylaminouracil (7.89 g).

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. customthe reaction was quenched by the addition of water (150 ml)
  3. extractionextracted with ethyl acetate (3×125 ml)
  4. washThe combined extracts were washed with water (2×50 25 ml), with saturated aqueous sodium chloride solution (50 ml)
  5. dry with materialdried over magnesium 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-774cc50a15de43b19d27a9b93958f27b
Quelldatensatz
uspto-grants-2004_08
Patentnummer
US06774130B2

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