Ethanol → 9-Hydroxy-6-phthalimidopurine

HRID 373896

Reaktionsgleichung

Reaktionsgleichung von HRID 373896
C([O:8][N:9]1[CH:17]=[N:16][C:15]2[C:10]1=[N:11][CH:12]=[N:13][C:14]=2[N:18]1[C:22](=[O:23])[C:21]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]2[C:19]1=[O:28])C1C=CC=CC=1.C(O)C>[Pd].O1CCCC1>[OH:8][N:9]1[CH:17]=[N:16][C:15]2[C:10]1=[N:11][CH:12]=[N:13][C:14]=2[N:18]1[C:22](=[O:23])[C:21]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]2[C:19]1=[O:28]

Komponenten

5

Edukt 2

HCID 702EthanolHCID 145239699-Benzyloxy-6-phthalimidopurine

Produkt 1

HCID 145239709-Hydroxy-6-phthalimidopurineAusbeute 83,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

A mixture of 9-benzyloxy-6-phthalimidopurine (11.0 g, 29.5 mmol), 10% palladium on charcoal (2.2 g), ethanol (300 ml) and tetrahydrofuran (500 ml) was stirred at 25° C. for 1 hour under an atmosphere of hydrogen. The suspension was then filtered and the catalyst washed with ethanol. The filtrate was evaporated under reduced pressure and the resulting solid triturated with ether. The solid was collected and then dried to afford the title compound (6.93 g; 83%). IR: υmax (KBr). 2607, 1794, 1735, 1603, 1582, 1467, 1401 cm-1 ; 1H NMRδH [(CD3)2SO] 8.15(4H, s, Ar), 8.95(1H, s, H-2), 9.15(1H, s, H-8), 12.80(1H, br.s, D2O exchangeable, OH). Found: C, 55.34; H, 2.58; N, 24.56%. C13H7N5O3 requires: C, 55.51; H, 2.51; N, 24.91%.

Aufarbeitung

  1. filtrationThe suspension was then filtered
  2. washthe catalyst washed with ethanol
  3. customThe filtrate was evaporated under reduced pressure
  4. customthe resulting solid triturated with ether
  5. customThe solid was collected
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-937fbcbfd5904517a73cca894d1872c7
Quelldatensatz
uspto-grants-1992_11
Patentnummer
US05166198

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