2-Bromopropane → 2-isopropylsulfanyl-3-(2-methoxy-phenyl)-7-methyl-3H-quinazolin-4-one

HRID 574320Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 574320
[CH:1](Br)([CH3:3])[CH3:2].[SH:5][C:6]1[N:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:22][CH3:23])[C:14](=[O:24])[C:13]2[C:8](=[CH:9][C:10]([CH3:25])=[CH:11][CH:12]=2)[N:7]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH:1]([S:5][C:6]1[N:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:22][CH3:23])[C:14](=[O:24])[C:13]2[C:8](=[CH:9][C:10]([CH3:25])=[CH:11][CH:12]=2)[N:7]=1)([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 178489574HCID 178489574, Verbindung

Produkt 1

HCID 444784282-isopropylsulfanyl-3-(2-methoxy-phenyl)-7-methyl-3H-quinazolin-4-oneAusbeute 59,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

Isopropyl bromide (0.11 mL, 1.25 mmol) was added to a suspension of 2-mercapto-3-(2-methoxy-phenyl)-7-methyl-3H-quinazolin-4-one (250 mg, 0.84 mmol) and potassium carbonate (235 mg, 1.68 mmol) in acetone (10 mL) and the mixture was heated at reflux for 16 hr. The reaction mixture was cooled to room temperature and the any solid were filtered and washed with acetone. The filtrate was concentrated to dryness in vacuo and the crude compound was purified by column chromatography over silica gel (100-200 mesh) using 5% ethyl acetate in pet ether as eluent to afford 2-isopropylsulfanyl-3-(2-methoxy-phenyl)-7-methyl-3H-quinazolin-4-one (170 mg, 59%) as semi solid.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 16 hr
  3. filtrationthe any solid were filtered
  4. washwashed with acetone
  5. concentrationThe filtrate was concentrated to dryness in vacuo
  6. customthe crude compound was purified by column chromatography over silica gel (100-200 mesh)

Quellen und Nachweise

ORD-Eintrag
ord-3512dd9fb24f4cd9952cb5cd14f5bf25
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09034887B2

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