Hydrochloric Acid → 7-(2,4-Dimethoxybenzyl)-2-thioxo-3-[4-(2,2,2-trifluoroethoxy)phenyl]-1,2,3,7-tetrahydropyrido[3,4-d]pyrimidine-4,8-dione

HRID 570731Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 570731
[N:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]([F:15])([F:14])[F:13])=[CH:6][CH:5]=1)=[C:2]=[S:3].[H-].[Na+].[NH2:18][C:19]1[C:20](=[O:41])[N:21]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][C:32]=2[O:39][CH3:40])[CH:22]=[CH:23][C:24]=1[C:25](OCC)=[O:26].Cl>CN(C)C=O>[CH3:40][O:39][C:32]1[CH:33]=[C:34]([O:37][CH3:38])[CH:35]=[CH:36][C:31]=1[CH2:30][N:21]1[CH:22]=[CH:23][C:24]2[C:25](=[O:26])[N:1]([C:4]3[CH:5]=[CH:6][C:7]([O:10][CH2:11][C:12]([F:13])([F:15])[F:14])=[CH:8][CH:9]=3)[C:2](=[S:3])[NH:18][C:19]=2[C:20]1=[O:41]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 866436111-Isothiocyanato-4-(2,2,2-trifluoroethoxy)benzeneHCID 86685389Ethyl 3-amino-1-(2,4-dimethoxybenzyl)-2-oxo-1,2-dihydropyridine-4-carboxylate

Produkt 1

HCID 866853907-(2,4-Dimethoxybenzyl)-2-thioxo-3-[4-(2,2,2-trifluoroethoxy)phenyl]-1,2,3,7-tetrahydropyrido[3,4-d]pyrimidine-4,8-dioneAusbeute 63,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 1-isothiocyanato-4-(2,2,2-trifluoroethoxy)benzene (375 mg) in N,N-dimethylformamide (5 ml) was added sodium hydride (60% in oil, 193 mg) under ice-cooling, and the mixture was cooled to 0° C. A solution of ethyl 3-amino-1-(2,4-dimethoxybenzyl)-2-oxo-1,2-dihydropyridine-4-carboxylate (535 mg) in N,N-dimethylformamide (5 ml) was added dropwise thereto, and the mixture was stirred at 0° C. for 15 min. The reaction mixture was poured into 0.3M hydrochloric acid (15 ml), and the precipitate was collected by filtration. The obtained solid was suspended in toluene, and the suspension was concentrated under reduced pressure. The residue was washed with diisopropyl ether to give the title compound (527 mg).

Aufarbeitung

  1. temperaturecooling
  2. filtrationthe precipitate was collected by filtration
  3. concentrationthe suspension was concentrated under reduced pressure
  4. washThe residue was washed with diisopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-9845ff307b6347c68c52d540f686e165
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09023858B2

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