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Sodium Hydroxide → HCID 22258014, Verbindung

HRID 1251591
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1251591
[CH3:1][N:2]1[C:7](=[O:8])[C:6]2[C:9]([S:23][C:24]3[CH:29]=[CH:28][C:27]([N+:30]([O-])=O)=[CH:26][CH:25]=3)=[C:10]([CH2:12][C:13]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH:16]=[CH:15][CH:14]=3)[S:11][C:5]=2[N:4]([CH2:33][CH:34]([CH3:36])[CH3:35])[C:3]1=[O:37].[Cl-].[NH4+].[OH-].[Na+]>C(O)C.O.[Fe]>[NH2:30][C:27]1[CH:28]=[CH:29][C:24]([S:23][C:9]2[C:6]3[C:7](=[O:8])[N:2]([CH3:1])[C:3](=[O:37])[N:4]([CH2:33][CH:34]([CH3:36])[CH3:35])[C:5]=3[S:11][C:10]=2[CH2:12][C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[CH:15][CH:14]=2)=[CH:25][CH:26]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 22257984HCID 22257984, Verbindung

Produkt 1

HCID 22258014HCID 22258014, VerbindungAusbeute 5,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23925IronKatalysator
HCID 702
Ethanol
Lösungsmittel
HCID 962WaterLösungsmittel

Versuchsvorschrift

A suspension of the crude 3-methyl-1-(2-methylpropyl)-6-(1-naphthalenylmethyl)-5-[(4-nitrophenyl)thio]thieno[2,3-d]pyrimidine-2,4-(1H, 3H)-dione (Example 35, 1.26 g), iron powder (0.59 g) and ammonium chloride (0.56 g) in ethanol (5 ml) and water (5 ml) was heated at reflux for 4 hours, then cooled to room temperature. Sodium hydroxide solution (10%, 50 ml) was added and the mixture was stirred for 1 hour. The resulting solution was decanted from insoluble solid. The solid and solution were in turn extracted with dichloromethane (3×50 ml) then ethyl acetate (3×50 ml). The combined organic extracts were dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The residue was partially purified by column chromatography over silica, eluting with ethyl acetate:isohexane (1:1). Some pure material was recrystallised from isohexane: ethyl acetate to give the title compound (0.065 g). The remaining material was purified by preparative normal-phase HPLC with dichloromethane:ethanol gradient elution to give the title compound (0.163 g).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. customThe resulting solution was decanted from insoluble solid
  4. extractionextracted with dichloromethane (3×50 ml)
  5. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe residue was partially purified by column chromatography over silica
  9. washeluting with ethyl acetate:isohexane (1:1)
  10. customSome pure material was recrystallised from isohexane

Quellen und Nachweise

ORD-Eintrag
ord-4ab24c6258f845a392f500726e4e3e3a
Quelldatensatz
uspto-grants-2002_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06342502B1

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