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

HRID 631348Notes

Reaction equation

HRID 631348 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 76.2%

Reagents, catalysts & solvents 1

HCID 80192-MethoxyethanolSolvent

Conditions

Temperature
130 °C

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-48114d9cfac141f69b4c770434472239
Source dataset
uspto-grants-2016_04
Patent number
US09320739B2

Reaction notes

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