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Trifluoroacetic acid → 7-(4-Diethylamino-butylamino)-3-(3,5-dimethoxy-phenyl)-1-ethyl-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one

HRID 1783536
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1783536
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:11]2[CH2:20][C:19]3[C:14](=[N:15][C:16](S(C)=O)=[N:17][CH:18]=3)[N:13]([CH2:24][CH3:25])[C:12]2=[O:26])[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.[CH2:27]([N:29]([CH2:35][CH3:36])[CH2:30][CH2:31][CH2:32][CH2:33][NH2:34])[CH3:28].FC(F)(F)C(O)=O>C(#N)C>[CH2:27]([N:29]([CH2:35][CH3:36])[CH2:30][CH2:31][CH2:32][CH2:33][NH:34][C:16]1[N:15]=[C:14]2[N:13]([CH2:24][CH3:25])[C:12](=[O:26])[N:11]([C:5]3[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=3)[CH2:20][C:19]2=[CH:18][N:17]=1)[CH3:28]
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Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 117976N,N-Diethyl-1,4-butanediamineHCID 68858127HCID 68858127, Verbindung

Produkt 1

HCID 540506487-(4-Diethylamino-butylamino)-3-(3,5-dimethoxy-phenyl)-1-ethyl-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-oneAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342
Acetonitrile
Lösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A mixture of 3-(3,5-dimethoxy-phenyl)-1-ethyl-7-methanesulfinyl-3,4-dihydro-pyrimido[4,5-d]pyrimidin-2(1H)-one (0.5 g, 1.33 mmol), 4-diethylaminobutylamine (0.38 g, 2.66 mmol,) and trifluoroacetic acid (0.31 g, 2.66 mmol) in acetonitrile (6 mL) was heated in a sealed tube at 90° C. for 18 hours. The solvent was removed under reduced pressure and the residue taken up in 1N HCl. The solution was made basic with 50% NaOH and extracted twice with dichloromethane. The combined organic layers were dried over magnesium sulfate, filtered, and evaporated. The residue was purified by radial chromatography eluting with a solvent mixture of ethyl acetate/methanol/ethyl (89:10:1 v/v/v) to give 0.34 g (56%) of the titled compound: mp 83-85° C. Mass Spectrum (APCI, 80/20 CH3CN/H2O, Probe=450° C.) (m+1)/z 458.2

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. extractionextracted twice with dichloromethane
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by radial chromatography
  7. washeluting with a solvent mixture of ethyl acetate/methanol/ethyl (89:10:1 v/v/v)

Quellen und Nachweise

ORD-Eintrag
ord-cf021851595c400e8dd96764b8eda5ba
Quelldatensatz
uspto-grants-2009_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07501425B1

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