Methanol → 4-(3,4-Dimethoxyphenyl)-2-(2-hydroxyethyl)-6,7-dimethoxyquinazoline

HRID 266121Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 266121
CO.[CH3:3][O:4][C:5]1[CH:6]=[C:7]([C:13]2[C:22]3[C:17](=[CH:18][C:19]([O:25][CH3:26])=[C:20]([O:23][CH3:24])[CH:21]=3)[N:16]=[C:15]([CH2:27][C:28](OC)=[O:29])[N:14]=2)[CH:8]=[CH:9][C:10]=1[O:11][CH3:12].[BH4-].[Na+].O1CCCC1>O>[CH3:3][O:4][C:5]1[CH:6]=[C:7]([C:13]2[C:22]3[C:17](=[CH:18][C:19]([O:25][CH3:26])=[C:20]([O:23][CH3:24])[CH:21]=3)[N:16]=[C:15]([CH2:27][CH2:28][OH:29])[N:14]=2)[CH:8]=[CH:9][C:10]=1[O:11][CH3:12]

Komponenten

6

Edukt 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 212240726,7-Dimethoxy-4-(3,4-dimethoxyphenyl)quinazoline-2-acetic acid methyl ester

Produkt 1

HCID 220975944-(3,4-Dimethoxyphenyl)-2-(2-hydroxyethyl)-6,7-dimethoxyquinazolineAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Methanol (15 ml) was added dropwise to a mixture of methyl 4-(3,4-dimethoxyphenyl)-6,7-dimethoxyquinazoline-2-acetate (4.0 g), sodium borohydride (1.9 g) and tetrahydrofuran (80 ml) under reflux. The mixture was stirred under reflux for 2 hours, and then poured into water, and extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried over magnesium sulfate. Evaporation of the solvent gave 4-(3,4-dimethoxyphenyl)-2-(2-hydroxyethyl)-6,7-dimethoxyquinazoline (3.0 g, 81%). This was recrystallized from ethyl acetate. Colorless needles, mp. 165°-166° C.

Aufarbeitung

  1. temperatureunder reflux
  2. temperatureunder reflux for 2 hours
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. customEvaporation of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-be8bbc0e4b694cb4b8ea6509d2d11b45
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05650410

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