Dimethylformamide → 3-butyl-6-ethyl-1-{[2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

HRID 1889440Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1889440
[CH2:1]([N:5]1[C:10](=[O:11])[C:9]2[CH:12]=[C:13]([CH2:15][CH3:16])[S:14][C:8]=2[NH:7][C:6]1=[O:17])[CH2:2][CH2:3][CH3:4].Br[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[C:32]2[N:36]=[C:35](C(Cl)(Cl)Cl)[O:34][N:33]=2)=[CH:22][CH:21]=1.CN(C)C=[O:44].[H-].[Na+]>C(OCC)(=O)C>[CH2:1]([N:5]1[C:10](=[O:11])[C:9]2[CH:12]=[C:13]([CH2:15][CH3:16])[S:14][C:8]=2[N:7]([CH2:19][C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[C:32]3[NH:36][C:35](=[O:44])[O:34][N:33]=3)=[CH:22][CH:21]=2)[C:6]1=[O:17])[CH2:2][CH2:3][CH3:4]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 15290996HCID 15290996, VerbindungHCID 593517803-butyl-6-ethylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

Produkt 1

HCID 1360523983-butyl-6-ethyl-1-{[2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl}thieno[2,3-d]pyrimidine-2,4(1H,3H)-dioneAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a mixture of 3-butyl-6-ethylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (1 g), 3-[4′-(bromomethyl)biphenyl-2-yl]-5-(trichloromethyl)-1,2,4-oxadiazole (1.89 g) and N,N-dimethylformamide (50 mL) was added sodium hydride (0.17 g), and the mixture was stirred at 50° C. for 1 hr. The reaction mixture was diluted with ethyl acetate, washed successively with 5% aqueous potassium hydrogensulfate solution and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. To the obtained residue was added 1N aqueous sodium hydroxide solution (50 mL), and the mixture was stirred at 60° C. for 1 hr. The reaction mixture was adjusted to pH 4 with 1N hydrochloric acid, extracted with ethyl acetate. The obtained ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography, and the obtained solid was recrystallized from tetrahydrofuran-diisopropylether to give the title compound as colorless crystals (1.13 g, 58%).

Aufarbeitung

  1. washwashed successively with 5% aqueous potassium hydrogensulfate solution and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. additionTo the obtained residue was added 1N aqueous sodium hydroxide solution (50 mL)
  5. stirringthe mixture was stirred at 60° C. for 1 hr
  6. extractionextracted with ethyl acetate
  7. washThe obtained ethyl acetate layer was washed with saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customThe solvent was evaporated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography
  11. customthe obtained solid was recrystallized from tetrahydrofuran-diisopropylether

Quellen und Nachweise

ORD-Eintrag
ord-cc66c0710ab84a14936625eace6d92b8
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08501750B2

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