Ethanol → 7-benzyl-8-ethoxy-3-ethyl-1-(3-hydroxypropyl)-1H-purine-2,6(3H,7H)-dione

HRID 2200565Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2200565
[Na].[CH2:2]([N:9]1[C:17]2[C:16](=[O:18])[N:15]([CH2:19][CH2:20][CH2:21][OH:22])[C:14](=[O:23])[N:13]([CH2:24][CH3:25])[C:12]=2[N:11]=[C:10]1Cl)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:27]([OH:29])[CH3:28]>>[CH2:2]([N:9]1[C:17]2[C:16](=[O:18])[N:15]([CH2:19][CH2:20][CH2:21][OH:22])[C:14](=[O:23])[N:13]([CH2:24][CH3:25])[C:12]=2[N:11]=[C:10]1[O:29][CH2:27][CH3:28])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Komponenten

4

Edukt 3

HCID 702EthanolHCID 5360545Sodium2×HCID 904030297-benzyl-8-chloro-3-ethyl-1-(3-hydroxypropyl)-1H-purine-2,6(3H,7H)-dione

Produkt 1

HCID 904023587-benzyl-8-ethoxy-3-ethyl-1-(3-hydroxypropyl)-1H-purine-2,6(3H,7H)-dioneAusbeute 77,9 %

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

A solution of sodium (50 mg, 2.17 mmol) in ethyl alcohol (10 mL) was stirred at 40° C. under nitrogen until the sodium was consumed. Then 7-benzyl-8-chloro-3-ethyl-1-(3-hydroxypropyl)-1H-purine-2,6(3H,7H)-dione (150 mg, 0.414 mmol) was added at 0° C. and the mixture was stirred at 40° C. for 4 h. The mixture was quenched with ice-water (15 mL) and concentrated. The aqueous residue was extracted with ethyl acetate. The organic phase was dried over sodium sulfate, filtered and concentrated to give 7-benzyl-8-ethoxy-3-ethyl-1-(3-hydroxypropyl)-1H-purine-2,6(3H,7H)-dione (120 mg, 77.9% yield) as yellow solid. LCMS retention time 1.488 min; LCMS MH+ 373.

Aufarbeitung

  1. customwas consumed
  2. customThe mixture was quenched with ice-water (15 mL)
  3. concentrationconcentrated
  4. extractionThe aqueous residue was extracted with ethyl acetate
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-8349567f587a4b4d8b239239ba093543
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09359359B2

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