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Sodium hydride → HCID 86685408, Verbindung

HRID 570751
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 570751
[S:1]=[C:2]1[NH:7][C:6]2=[CH:8][S:9][CH:10]=[C:5]2[C:4](=[O:11])[N:3]1[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20]([F:23])([F:22])[F:21])=[CH:14][CH:13]=1.[H-].[Na+].[C:26]([O:30][C:31](=[O:36])[NH:32][CH2:33][CH2:34]Br)([CH3:29])([CH3:28])[CH3:27].[Cl-].[NH4+]>CN(C)C=O>[O:11]=[C:4]1[N:3]([C:12]2[CH:13]=[CH:14][C:15]([O:18][CH2:19][C:20]([F:22])([F:23])[F:21])=[CH:16][CH:17]=2)[C:2]([S:1][CH2:34][CH2:33][NH:32][C:31](=[O:36])[O:30][C:26]([CH3:29])([CH3:28])[CH3:27])=[N:7][C:6]2=[CH:8][S:9][CH:10]=[C:5]12
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 86685406HCID 86685406, Verbindung

Produkt 1

HCID 86685408HCID 86685408, VerbindungAusbeute 95,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Versuchsvorschrift

2-Thioxo-3-[4-(2,2,2-trifluoroethoxy)phenyl]-2,3-dihydrothieno[3,4-d]pyrimidin-4(1H)-one (1.59 g) was dissolved in N,N-dimethylformamide (20 ml), sodium hydride (60% in oil, 0.25 g) and tert-butyl(2-bromoethyl)carbamate (1.49 g) were added successively thereto under ice-cooling, and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was poured into saturated aqueous ammonium chloride solution (30 ml), and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) to give the title compound (2.12 g) as a white solid.

Aufarbeitung

  1. temperatureunder ice-cooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-27e42f2c43aa42109488cf5f8e66f94c
Quelldatensatz
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09023858B2

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