Dimethyl Sulfoxide → 3-Methyl-7-(methylpivaloyl)xanthine

HRID 361482

Reaktionsgleichung

Reaktionsgleichung von HRID 361482
[CH3:1][N:2]1[C:10]2[N:9]=[CH:8][NH:7][C:6]=2[C:5](=[O:11])[NH:4][C:3]1=[O:12].[H-].[Na+].CS(C)=O.Cl[CH2:20][CH2:21][C:22]([CH3:27])([CH3:26])[C:23]([O-])=[O:24]>O>[CH3:1][N:2]1[C:10]2[N:9]=[CH:8][N:7]([C:23](=[O:24])[C:22]([CH3:27])([CH3:26])[CH2:21][CH3:20])[C:6]=2[C:5](=[O:11])[NH:4][C:3]1=[O:12]

Komponenten

6

Edukt 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 706393-MethylxanthineHCID 217530474-Chloro-2,2-dimethylbutanoate

Produkt 1

HCID 215842333-Methyl-7-(methylpivaloyl)xanthineAusbeute 90,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

This example illustrates a synthesis of 1-(11,10-Oxidoundecanyl)-3-methyl-7-methylpivalylxanthine (inventive compound no. 1412). A mixture of 3-methylxanthine (Aldrich, 1.00 g, 6.0 mmol), sodium hydride (145 mg, 6.0 mmol) and dimethyl sulfoxide (20 mL) was stirred until homogeneous (0.5 hours). Chloromethylpivalate (865 mL, 904 mg, 6.0 mmol) was added and the reaction stirred for 18 hours. The reaction mixture was poured into water (70 mL) and then extracted with 25% ethano/dichloromethane (4×60 mL). The combined organic extracts were dried over sodium sulfate and evaporated under vacuum to a volume of 40 mL. This solution was cooled in icewater, whereupon a thick white precipitate formed. The solid was filtered off under suction and dried under vacuum to yield 1.43 g (90% yield) 3-methyl-7-(methylpivaloyl)xanthine (inventive compound no. 1404).

Aufarbeitung

  1. stirringthe reaction stirred for 18 hours
  2. extractionextracted with 25% ethano/dichloromethane (4×60 mL)
  3. dry with materialThe combined organic extracts were dried over sodium sulfate
  4. customevaporated under vacuum to a volume of 40 mL
  5. temperatureThis solution was cooled in icewater, whereupon a thick white precipitate
  6. customformed
  7. filtrationThe solid was filtered off under suction
  8. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-2177ddf5787b4adfb9a33a5cc43679ce
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05866576

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