Theophylline → Diethyl [4-(1,3-dimethylxanthin-7-yl)butyl]phosphonate

HRID 1985

Reaktionsgleichung

Reaktionsgleichung von HRID 1985
[CH3:1][N:2]1[C:11](=[O:12])[C:10]2[NH:9][CH:8]=[N:7][C:6]=2[N:5]([CH3:13])[C:3]1=[O:4].Cl[CH2:15][CH2:16][CH2:17][CH2:18][P:19]([O:24][CH2:25][CH3:26])(=[O:23])[O:20][CH2:21][CH3:22].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:1][N:2]1[C:11](=[O:12])[C:10]2[N:9]([CH2:15][CH2:16][CH2:17][CH2:18][P:19](=[O:23])([O:24][CH2:25][CH3:26])[O:20][CH2:21][CH3:22])[CH:8]=[N:7][C:6]=2[N:5]([CH3:13])[C:3]1=[O:4]

Komponenten

5

Edukt 3

HCID 2153TheophyllineHCID 11430Potassium CarbonateHCID 19689195Diethyl(4-chlorobutyl)phosphonate

Produkt 1

HCID 22446301Diethyl [4-(1,3-dimethylxanthin-7-yl)butyl]phosphonate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

10.9 g (0.05 mol) of 1,3-dimethylxanthine were suspended in 150 ml of DMF, treated with 13.7 g (0.06 mol) of diethyl 4-chlorobutanephosphonate and 7.0 g (0.05 mol) of activated potassium carbonate and heated at 70° C. for approximately 4 hours. The solid was then filtered off, the filtrate was concentrated under reduced pressure and the oily residue which remained was taken up in ethyl acetate, filtered again and crystallized from diisopropyl ether.

Aufarbeitung

  1. filtrationThe solid was then filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. filtrationfiltered again
  4. customcrystallized from diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-126b62e8f9c14b19bd96ee46b744d0b7
Quelldatensatz
uspto-grants-1998_03
Patentnummer
US05728686

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