StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Triethylamine → 6-cyclopropyl-3-(2,4-dimethoxybenzyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

HRID 1889343
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1889343
[NH2:1][C:2]1[S:3][C:4]([CH:11]2[CH2:13][CH2:12]2)=[CH:5][C:6]=1[C:7]([O:9]C)=O.Cl[C:15](Cl)([O:17]C(=O)OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C.[CH3:33][O:34][C:35]1[CH:40]=[C:39]([O:41][CH3:42])[CH:38]=[CH:37][C:36]=1[CH2:43][NH2:44]>C(Cl)Cl>[CH:11]1([C:4]2[S:3][C:2]3[NH:1][C:15](=[O:17])[N:44]([CH2:43][C:36]4[CH:37]=[CH:38][C:39]([O:41][CH3:42])=[CH:40][C:35]=4[O:34][CH3:33])[C:7](=[O:9])[C:6]=3[CH:5]=2)[CH2:13][CH2:12]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 5972502,4-DimethoxybenzylamineHCID 45089420Methyl 2-amino-5-cyclopropylthiophene-3-carboxylate

Produkt 1

HCID 593517456-cyclopropyl-3-(2,4-dimethoxybenzyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dioneAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution (300 mL) of methyl 2-amino-5-cyclopropylthiophene-3-carboxylate (4.7 g) in methylene chloride were added triphosgene (3.06 g) and triethylamine (8.6 mL), and the mixture was stirred at room temperature for 2 hr. To the reaction mixture was added 1-(2,4-dimethoxyphenyl)methanamine (7.2 mL), and the mixture was further stirred at room temperature for 1 hr. The reaction mixture was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was dissolved in methanol (300 mL), sodium methoxide (6.4 g) was added, and the mixture was stirred at 60° C. for 2 hr. The reaction mixture was concentrated under reduced pressure, and the obtained residue was extracted with 1N hydrochloric acid and chloroform. The chloroform layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The precipitated solid was collected by filtration to give the title compound as a colorless solid (8.53 g, 100%).

Aufarbeitung

  1. stirringthe mixture was further stirred at room temperature for 1 hr
  2. washThe reaction mixture was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. dissolutionThe obtained residue was dissolved in methanol (300 mL)
  6. additionsodium methoxide (6.4 g) was added
  7. stirringthe mixture was stirred at 60° C. for 2 hr
  8. concentrationThe reaction mixture was concentrated under reduced pressure
  9. extractionthe obtained residue was extracted with 1N hydrochloric acid and chloroform
  10. washThe chloroform layer was washed with saturated brine
  11. dry with materialdried over anhydrous magnesium sulfate
  12. customThe solvent was evaporated under reduced pressure
  13. filtrationThe precipitated solid was collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-df61078afda04cde92f4d5ffa24f2645
Quelldatensatz
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08501750B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion