Benzene, 1-(chloromethyl)-2-fluoro- → Methyl 3-(2-flourobenzyl)-4-oxo-3,4-dihydroquinazoline-7-carboylate

HRID 1094733Notes

Reaction equation

HRID 1094733 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:10]=2)[N:5]=[CH:4][NH:3]1.C([O-])([O-])=O.[K+].[K+].[F:22][C:23]1[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=1[CH2:25]Cl>C(#N)C>[F:22][C:23]1[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=1[CH2:25][N:3]1[C:2](=[O:1])[C:11]2[C:6](=[CH:7][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:10]=2)[N:5]=[CH:4]1

Participants

5

Reactant 3

HCID 9580Benzene, 1-(chloromethyl)-2-fluoro-HCID 11430Potassium CarbonateHCID 135481487Methyl 4-hydroxyquinazoline-7-carboxylate

Product 1

HCID 59842874Methyl 3-(2-flourobenzyl)-4-oxo-3,4-dihydroquinazoline-7-carboylateYield 70%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Methyl 4-oxo-3,4-dihydroquinazoline-7-carboxlate 300 mg (1.37 mmol) was dissolved in acetonitrile (20 mL) followed by addition of K2CO3 (100 mg), KI (80 mg) and 2-flourobenzyl chloride (0.2 mL, 1.65 mmol). The mixture was refluxed over night. The reaction mixture was concentrated and the residue was purified by flash chromatography (Et2O:DCM, 1:1) to give methyl 3-(2-flourobenzyl)4-oxo-3,4-dihydroquinazoline-7-carboxylate in 70% yield.

Workup

  1. temperatureThe mixture was refluxed over night
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was purified by flash chromatography (Et2O:DCM, 1:1)

Sources & evidence

ORD record
ord-bfc1335746724a1f9365c954d7425f69
Source dataset
uspto-grants-2012_03
Patent number
US08133998B2

Reaction notes

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