Formamidine acetate → 5,7-dimethoxyquinazolin-4(3H)-one

HRID 871393Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 871393
[NH2:1][C:2]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[C:8]([O:14][CH3:15])[C:3]=1[C:4](OC)=[O:5].C(O)(=O)C.[CH:20](N)=[NH:21]>COCCO>[CH3:15][O:14][C:8]1[CH:9]=[C:10]([O:12][CH3:13])[CH:11]=[C:2]2[C:3]=1[C:4](=[O:5])[NH:21][CH:20]=[N:1]2

Komponenten

4

Edukt 2

HCID 160693Formamidine acetateHCID 11550253Methyl 2-amino-4,6-dimethoxybenzoate

Produkt 1

HCID 1355106675,7-dimethoxyquinazolin-4(3H)-oneAusbeute 76,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80192-MethoxyethanolLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A mixture of methyl 2-amino-4,6-dimethoxybenzoate (6.46 g, 30.6 mmol), formamidine acetate (15.92 g, 153 mmol) in 2-methoxyethanol (50 mL) was heated at 130° C. for 4 hours. After the solvent was removed under reduced pressure, the reaction was quenched with water, filtered, washed with water, and dried under vacuum with P2O5 to afford 5,7-dimethoxyquinazolin-4(3H)-one as a solid (4.805 g, 76%). 1H NMR (300 MHz, DMSO-d6) δ 11.7 (br, 1H), 7.98 (s, 1H), 6.72 (d, 1H), 6.60 (d, 1H), 3.92 (s, 3H), 3.88 (s, 3H); LC-MS (ESI) m/z 207 (M+H)+.

Aufarbeitung

  1. customAfter the solvent was removed under reduced pressure
  2. customthe reaction was quenched with water
  3. filtrationfiltered
  4. washwashed with water
  5. dry with materialdried under vacuum with P2O5

Quellen und Nachweise

ORD-Eintrag
ord-11b36be9c27c4f089ce86686ca9a7723
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969587B2

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