Dimethyl Sulfone → Methyl 2-amino-4-oxo-3,4-dihydroquinazoline-7-carboxylate

HRID 1616125Notes

Reaction equation

HRID 1616125 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[CH:9]=[CH:8][C:3]=1[C:4](OC)=[O:5].Cl.[C:17](Cl)(=[NH:19])[NH2:18].CS(C)(=O)=O>O>[NH2:18][C:17]1[NH:19][C:4](=[O:5])[C:3]2[C:2](=[CH:11][C:10]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:8]=2)[N:1]=1

Participants

5

Reactant 3

HCID 6213Dimethyl SulfoneHCID 79336Dimethyl aminoterephthalateHCID 3084509Chloroformamidinium chloride

Product 1

HCID 136346397Methyl 2-amino-4-oxo-3,4-dihydroquinazoline-7-carboxylateYield 95%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

Into a round bottom flask was added dimethyl 2-aminoterephthalate (1.0 g, 4.8 mmol) mixed with carbamimidic chloride-HCl (1.10 g, 9.6 mmol) and dimethyl sulfone (4.5 g, 47.8 mmol). The reaction mixture was heated to 150° C. and stirred overnight. The mixture was cooled to rt, water added and the solid was filtered. The solid was then washed with acetic acid to afford methyl 2-amino-4-oxo-3,4-dihydroquinazoline-7-carboxylate (1.0 g, 95%). LC-MS: (FA) ES+ 220.

Workup

  1. temperatureThe mixture was cooled to rt
  2. filtrationthe solid was filtered
  3. washThe solid was then washed with acetic acid

Sources & evidence

ORD record
ord-64309a5ae48840b5b30a06d6c50d89f2
Source dataset
uspto-grants-2014_07
Patent number
US08765773B2

Reaction notes

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