Methanol → 6-Ethyl-9-(4-hydroxyphenyl)-2-trifluoromethylpurine

HRID 2056249Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2056249
[CH2:1]([C:3]1[N:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[N:9]=[C:8]2[C:4]=1[N:5]=[CH:6][N:7]2[C:16]1[CH:21]=[CH:20][C:19]([O:22]CC2C=CC=CC=2)=[CH:18][CH:17]=1)[CH3:2].CO.[H][H]>[Pd].C(O)(=O)C>[CH2:1]([C:3]1[N:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[N:9]=[C:8]2[C:4]=1[N:5]=[CH:6][N:7]2[C:16]1[CH:17]=[CH:18][C:19]([OH:22])=[CH:20][CH:21]=1)[CH3:2]

Komponenten

6

Edukt 3

HCID 887MethanolHCID 104309696-Ethyl-9-(4-benzyloxyphenyl)-2-trifluoromethylpurineHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 103578946-Ethyl-9-(4-hydroxyphenyl)-2-trifluoromethylpurineAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A mixture of 6-ethyl-9-(4-benzyloxyphenyl)-2-trifluoromethylpurine (0.1 mmol), palladium on active carbon (0.001 mol, methanol (50 mL) and acetic acid (3 mL) was shaken under 30 psi hydrogen. After 5 hours, the reaction mixture was filtered through celite and the filtrate was concentrated under vacuum. The resulting residue was dissolved in 30 mL of ethyl acetate and washed with 5% aqueous sodium bicarbonate (1×30 mL). Concentration and Chromatography (5% methanol in dichloromethane) gave 6-ethyl-9-(4-hydroxyphenyl)-2-trifluoromethylpurine (21 mg, 93%). 1H NMR (300 MHz, CDCl3) δ 8.37 (s, 1H), 7.45 (d, J=7.2 Hz, 2H), 6.96 (d, J=7.2 Hz, 2H), 3.29 (q, J=7.5 Hz, 2 H), 3.11 (s, 1H), 1.41 (t, J=7.5 Hz, 3H). [ESMS m/z (309.4 (M+H)+)]

Aufarbeitung

  1. filtrationthe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated under vacuum
  3. dissolutionThe resulting residue was dissolved in 30 mL of ethyl acetate
  4. washwashed with 5% aqueous sodium bicarbonate (1×30 mL)
  5. concentrationConcentration and Chromatography (5% methanol in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-ab11025c73d6429a819fa33ba019d7d0
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07335654B2

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