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Water → 3-Desmethyl Istradefylline

HRID 1081844
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1081844
[OH:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[OH:26])/[CH:5]=[CH:6]/[C:7]1[N:15]([CH3:16])[C:14]2[C:13](=[O:17])[N:12]([CH2:18][CH3:19])[C:11](=[O:20])[N:10]([CH2:21][CH3:22])[C:9]=2[N:8]=1.CI.[C:29](=O)([O-])[O-].[Li+].[Li+].O>CN(C)C=O.C(Cl)(Cl)Cl>[CH2:18]([N:12]1[C:13](=[O:17])[C:14]2[N:15]([CH3:16])[C:7](/[CH:6]=[CH:5]/[C:4]3[CH:23]=[CH:24][C:25]([O:26][CH3:29])=[C:2]([OH:1])[CH:3]=3)=[N:8][C:9]=2[N:10]([CH2:21][CH3:22])[C:11]1=[O:20])[CH3:19]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 962WaterHCID 6328Methyl iodideHCID 11125Lithium Carbonate2×HCID 1357703383,4-Didesmethyl Istradefylline

Produkt 1

HCID 64489493-Desmethyl IstradefyllineAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212
Chloroform
Lösungsmittel
HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Compound 173 (400 mg, 1.12 mmol) obtained in Reference Example 112 was dissolved in 8 ml of dimethylformamide. To the solution were added 0.35 ml (5.62 mmol) of methyl iodide and 415 mg (5.62 mmol) of lithium carbonate, and the mixture was stirred at 80° C. for 3.5 hours. Water was added thereto to dissolve lithium carbonate, followed by addition of chloroform. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate, followed by evaporation under reduced pressure. The residue was purified by silica gel column chromatography (eluent:chloroform) to give 127 mg (yield 76%) of Compound 174 as a pale brown powder. The obtained crude crystals were further recrystallized from ethanol.

Aufarbeitung

  1. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  2. dry with materialdried over anhydrous sodium sulfate
  3. customfollowed by evaporation under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (eluent:chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-2b5b4050f4f14bfd96039e6b449c5bfb
Quelldatensatz
uspto-grants-1996_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05587378

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