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4-(2-(Diethylamino)ethoxy)aniline → 3-(2,6-dichlorophenyl)-1-[2-cyclohexen-1(RS)-yl]-7-[4-[2-(diethylamino)ethoxy]anilino]-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one

HRID 1858247
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1858247
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[CH2:18][C:17]2[C:12](=[N:13][C:14](S(C)(=O)=O)=[N:15][CH:16]=2)[N:11]([CH:23]2[CH2:28][CH2:27][CH2:26][CH:25]=[CH:24]2)[C:10]1=[O:29].[CH2:30]([N:32]([CH2:43][CH3:44])[CH2:33][CH2:34][O:35][C:36]1[CH:42]=[CH:41][C:39]([NH2:40])=[CH:38][CH:37]=1)[CH3:31]>ClCCl.CO.C(O)(=O)C.O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[CH2:18][C:17]2[C:12](=[N:13][C:14]([NH:40][C:39]3[CH:38]=[CH:37][C:36]([O:35][CH2:34][CH2:33][N:32]([CH2:43][CH3:44])[CH2:30][CH3:31])=[CH:42][CH:41]=3)=[N:15][CH:16]=2)[N:11]([CH:23]2[CH2:28][CH2:27][CH2:26][CH:25]=[CH:24]2)[C:10]1=[O:29]
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Komponenten

4

Edukt 2

HCID 4189324-(2-(Diethylamino)ethoxy)anilineHCID 221250623-(2,6-dichlorophenyl)-1-[2-cyclohexen-1(RS)-yl]-7-methanesulfonyl-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one

Produkt 1

HCID 221250143-(2,6-dichlorophenyl)-1-[2-cyclohexen-1(RS)-yl]-7-[4-[2-(diethylamino)ethoxy]anilino]-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-oneAusbeute 22 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 18914200
Dichloromethane methanol acetic acid water
Lösungsmittel

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

A mixture of 70 mg (0.15 mmol) of 3-(2,6-dichlorophenyl)-1-[2-cyclohexen-1(RS)-yl]-7-methanesulfonyl-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one and 150 mg (0.7 mmol) of 4-[2-(diethylamino)ethoxy]aniline was heated at 180° C. for 35 minutes and then cooled. The residue was subjected to column chromatography on silica gel using dichloromethane/methanol/acetic acid/water (240:24:3:2) for the elution. Product-containing fractions were combined and evaporated and the residue was evaporated with toluene. The residue was then dissolved in 30 ml of dichloromethane, washed twice with 20 ml of saturated aqueous sodium bicarbonate solution each time, dried over magnesium sulfate, filtered and evaporated to give 5 mg (22%) of 3-(2,6-dichlorophenyl)-1-[2-cyclohexen-1(RS)-yl]-7-[4-[2-(diethylamino)ethoxy]anilino]-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one as an orange colored gum. [Mass spectrum (ESI) MH+ =581].

Aufarbeitung

  1. temperaturecooled
  2. washfor the elution
  3. customevaporated
  4. customthe residue was evaporated with toluene
  5. dissolutionThe residue was then dissolved in 30 ml of dichloromethane
  6. washwashed twice with 20 ml of saturated aqueous sodium bicarbonate solution each time
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-d776d5854da742dd8ab5797cbba688da
Quelldatensatz
uspto-grants-2000_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06150373

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