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Sodium Hydroxide → HCID 22258014, Verbindung

HRID 1611032
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1611032
[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-85aed90b4329450c9ee3befc90e83d46
Quelldatensatz
uspto-grants-2006_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06984644B2

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