Acetic Acid → 7-Benzyl-3-butylxanthine

HRID 1943830

Reaktionsgleichung

Reaktionsgleichung von HRID 1943830
[CH2:1]([N:8]1[C:16]2[C:15](=[O:17])[NH:14][C:13](=[O:18])[NH:12][C:11]=2[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:25](I)[CH2:26][CH2:27][CH3:28].C(O)(=O)C>CN(C=O)C>[CH2:25]([N:12]1[C:11]2[N:10]=[CH:9][N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:16]=2[C:15](=[O:17])[NH:14][C:13]1=[O:18])[CH2:26][CH2:27][CH3:28]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 10962Butyl iodideHCID 11430Potassium CarbonateHCID 125005077-Benzyl-1H-purine-2,6(3H,7H)-dione

Produkt 1

HCID 39938667-Benzyl-3-butylxanthineAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

7-benzyl-3,7-dihydro-1H-purine-2,6-dione (17.14 g, 70.8 mmol) [Synthetic Communications, 20 (16), 2459-2467, 1990] and potassium carbonate (11.43 g, 82.8 mmol) were suspended in DMF (400 mL) at 40° C. After stirring for thirty minutes, butyl iodide (8.76 mL, 77.0 mmol) was added, and the mixture was stirred at 40° C. overnight. 50% Aqueous acetic acid (60 mL) was added, and the solution was concentrated under reduced pressure. The residue was suspended in water (500 mL), and the products were extracted into chloroform. The organics were collected, concentrated, and product was isolated using flash chromatography eluting with 1% methanol in dichloromethane to provide the product (9.49 g, 45%); 1H NMR (400 MHz; CDCl3) δ: 0.95 (3H, t), 1.34-1.41 (2H, m), 1.70-1.78 (2H, m), 4.05 (2H, t), 5.46 (2H, s), 7.31-7.40 (5H, m), 7.56 (1H, s), 8.21 (1H, br.s); m/z 299[MH+].

Aufarbeitung

  1. stirringthe mixture was stirred at 40° C. overnight
  2. concentrationthe solution was concentrated under reduced pressure
  3. extractionthe products were extracted into chloroform
  4. customThe organics were collected
  5. concentrationconcentrated
  6. customproduct was isolated
  7. washeluting with 1% methanol in dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-38c2a5011cae4dcc8b0a28ab57865716
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08394808B2

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