Potassium Carbonate → (Z)-2-(3-methoxy-4-(5-(2-methoxy-5-(3,4,5-trimethoxystyryl)phenoxy)pentyloxy)phenyl)-2,3-dihydroquinazolin-4(1H)-one

HRID 334323

Reaktionsgleichung

Reaktionsgleichung von HRID 334323
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]\[C:11]2[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[C:13]([O:21][CH3:22])[CH:12]=2)=[CH:5][C:4]=1[OH:23].C(=O)([O-])[O-].[K+].[K+].Br[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][O:36][C:37]1[CH:42]=[CH:41][C:40]([CH:43]2[NH:52][C:51](=[O:53])[C:50]3[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=3)[NH:44]2)=[CH:39][C:38]=1[O:54][CH3:55]>CN(C=O)C.C(OCC)(=O)C.CCCCCC>[CH3:55][O:54][C:38]1[CH:39]=[C:40]([CH:43]2[NH:52][C:51](=[O:53])[C:50]3[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=3)[NH:44]2)[CH:41]=[CH:42][C:37]=1[O:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][O:23][C:4]1[CH:5]=[C:6](/[CH:9]=[CH:10]\[C:11]2[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[C:13]([O:21][CH3:22])[CH:12]=2)[CH:7]=[CH:8][C:3]=1[O:2][CH3:1]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 5351344Combretastatin A4HCID 510425832-[4-(5-Bromo-pentyloxy)-3-methoxy-phenyl]-2,3-dihydro-1H-quinazolin-4-one

Produkt 1

HCID 117687597(Z)-2-(3-methoxy-4-(5-(2-methoxy-5-(3,4,5-trimethoxystyryl)phenoxy)pentyloxy)phenyl)-2,3-dihydroquinazolin-4(1H)-oneAusbeute 83,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 21226206Ethyl acetate hexaneLösungsmittel

Reaktionsbedingungen

Temperatur
30 °C

Versuchsvorschrift

(Z)-2-methoxy-5-(3,4,5-trimethoxystyryl)phenol (38a) (316.35 mg 1.0 mmol) in DMF (20 mL) was added anhydrous potassium carbonate (690 mg, 5.0 mmol) and 2-[4-(5-Bromo-pentyloxy)-3-methoxy-phenyl]-2,3-dihydro-1H-quinazolin-4-one (2d) (419.29 mg, 1.0 mmol). The reaction mixture was stirred at a temperature of 30° C. for 30 h and the reaction was monitored by TLC using ethyl acetate-hexane (6:4) as a solvent system. Then to this ice is added and extracted with ethyl acetate. The solvent was evaporated under vacuum to afford the crude product. This was further purified by column chromatography using ethyl acetate:hexane (6:4) as a solvent system to obtain the pure product (39d) (546 mg, 80% yield).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. customThe solvent was evaporated under vacuum
  3. customto afford the crude product
  4. customThis was further purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c2f30562fb904be4acfb5368de4957b3
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883809B2

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