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

HRID 641714Notes

Reaction equation

HRID 641714 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

HCID 1355106675,7-dimethoxyquinazolin-4(3H)-oneYield 92.8%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Procedure

A mixture of methyl 2-amino-4,6-dimethoxybenzoate (16 g), formamidine acetate (24 g) and 2-methoxyethanol (330 ml) was stirred and heated to reflux until all of the starting material had reacted. The mixture was evaporated and the residue was triturated under water (100 ml). The resultant solid was isolated, washed with water and dried under vacuum to give 5,7-dimethoxy-3,4-dihydroquinazolin-4-one (14.5 g); NMR Spectrum: (DMSOd6) 3.82 (s, 3H), 3.86 (s, 3H), 6.5 (s, 1H), 6.7 (s, 1H), 7.9 (s, 1H), 11.7 (br s, 1).

Workup

  1. temperatureheated
  2. temperatureto reflux until all of the starting material
  3. customhad reacted
  4. customThe mixture was evaporated
  5. customthe residue was triturated under water (100 ml)
  6. customThe resultant solid was isolated
  7. washwashed with water
  8. customdried under vacuum

Sources & evidence

ORD record
ord-21c186dee0fe4c17b3201d03ee672785
Source dataset
uspto-grants-2010_04
Patent number
US07696214B2

Reaction notes

Loading…