Sodium hydride → 4-(5-Benzylpyrazol-3-yloxy)-6-methoxy-7-(3-morpholinopropoxy)quinazoline

HRID 855672Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 855672
[CH2:1]([C:8]1[CH2:12][C:11](=[O:13])[NH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:17]1[C:26]2[C:21](=[CH:22][C:23]([O:29][CH2:30][CH2:31][CH2:32][N:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)=[C:24]([O:27][CH3:28])[CH:25]=2)[N:20]=[CH:19][N:18]=1>CN(C=O)C.[Cl-].[NH4+]>[CH2:1]([C:8]1[NH:9][N:10]=[C:11]([O:13][C:17]2[C:26]3[C:21](=[CH:22][C:23]([O:29][CH2:30][CH2:31][CH2:32][N:33]4[CH2:34][CH2:35][O:36][CH2:37][CH2:38]4)=[C:24]([O:27][CH3:28])[CH:25]=3)[N:20]=[CH:19][N:18]=2)[CH:12]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 3

HCID 24758Sodium hydrideHCID 118239414-Chloro-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazolineHCID 220592713-benzyl-1H-pyrazol-5(4H)-one

Produkt 1

HCID 179427484-(5-Benzylpyrazol-3-yloxy)-6-methoxy-7-(3-morpholinopropoxy)quinazolineAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 25517Ammonium ChlorideLösungsmittel

Versuchsvorschrift

3-Benzyl-4,5-dihydro-1H-pyrazol-5-one (174 mg, 1 mmol), (J. Chem. Soc. Perk. Trans 1, 1980, 1618-1621), was added to a suspension of sodium hydride (40 mg, 1 mmol, prewashed with pentane) in DMF (3 ml) under nitrogen. After stirring for 30 minutes at ambient temperature, 4-chloro-6-methoxy-7-(3-morpholinopropoxy)quinazoline (135 mg, 0.4 mmol) was added and the mixture was heated at 80° C for 1 hour. After cooling, the mixture was diluted with saturated aqueous ammonium chloride solution and partitioned between ethyl acetate and water. The precipitate was collected by filtration, washed with water, followed by ethanol, ether and dried under vacuum to give 4-(5-benzylpyrazol-3-yloxy)-6-methoxy-7-(3-morpholinopropoxy)quinazoline (150 mg, 79%).

Aufarbeitung

  1. temperaturethe mixture was heated at 80° C for 1 hour
  2. temperatureAfter cooling
  3. custompartitioned between ethyl acetate and water
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with water
  6. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-861d09854a0c4fa9811eae4b0e2e2452
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07262201B1

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