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4'-{[6-ethyl-3-(1-methyl-2-oxoethyl)-2,4-dioxo-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl]methyl}biphenyl-2-carbonitrile → 4'-{[6-ethyl-3-[2-hydroxy-2-(4-methoxyphenyl)-1-methylethyl]-2,4-dioxo-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl]methyl}biphenyl-2-carbonitrile

HRID 1889367
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1889367
[CH2:1]([C:3]1[S:32][C:6]2[N:7]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]4[C:25]([C:30]#[N:31])=[CH:26][CH:27]=[CH:28][CH:29]=4)=[CH:20][CH:19]=3)[C:8](=[O:16])[N:9]([CH:12]([CH3:15])[CH:13]=[O:14])[C:10](=[O:11])[C:5]=2[CH:4]=1)[CH3:2].[CH3:33][O:34][C:35]1[CH:40]=[CH:39][C:38]([Mg]Br)=[CH:37][CH:36]=1>O1CCCC1>[CH2:1]([C:3]1[S:32][C:6]2[N:7]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]4[C:25]([C:30]#[N:31])=[CH:26][CH:27]=[CH:28][CH:29]=4)=[CH:20][CH:19]=3)[C:8](=[O:16])[N:9]([CH:12]([CH3:15])[CH:13]([OH:14])[C:38]3[CH:39]=[CH:40][C:35]([O:34][CH3:33])=[CH:36][CH:37]=3)[C:10](=[O:11])[C:5]=2[CH:4]=1)[CH3:2]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 593515604'-{[6-ethyl-3-(1-methyl-2-oxoethyl)-2,4-dioxo-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl]methyl}biphenyl-2-carbonitrileHCID 178491912HCID 178491912, Verbindung

Produkt 1

HCID 593517204'-{[6-ethyl-3-[2-hydroxy-2-(4-methoxyphenyl)-1-methylethyl]-2,4-dioxo-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl]methyl}biphenyl-2-carbonitrileAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a mixture of 4′-{[6-ethyl-3-(1-methyl-2-oxoethyl)-2,4-dioxo-3,4-dihydrothieno[2,3-d]pyrimidin-1(2H)-yl]methyl}biphenyl-2-carbonitrile (1.7 g) and tetrahydrofuran (100 mL) was added 4-methoxyphenyl-magnesium bromide (12.6 mL), and the mixture was stirred at 50° C. for 16 hr. The reaction mixture was extracted with saturated aqueous ammonium chloride solution and ethyl acetate. The ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the title compound as a colorless amorphous solid (0.68 g, 32%).

Aufarbeitung

  1. extractionThe reaction mixture was extracted with saturated aqueous ammonium chloride solution and ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ff04d279ee54488b85529d9e3d3d4700
Quelldatensatz
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08501750B2

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