N,N-Dimethylaniline → 6-Bromo-4-chloro-2-(2-methoxyphenyl)quinazoline

HRID 2079292Notes

Reaction equation

HRID 2079292 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH3:19])[NH:6][C:5]2=O.O=P(Cl)(Cl)[Cl:23].CN(C)C1C=CC=CC=1>C1C=CC=CC=1.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH3:19])[N:6]=[C:5]2[Cl:23]

Participants

6

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 1361214046-Bromo-2-(2-methoxy-phenyl)-3h-quinazolin-4-one

Product 1

HCID 580109046-Bromo-4-chloro-2-(2-methoxyphenyl)quinazoline

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Procedure

6-Bromo-2-(2-methoxyphenyl)quinazolin-4(3H)-one (674 mg, 2.0 mmol), POCl3 (624 mg, 4 mmol), and N,N-dimethylaniline (740 mg, 6.1 mmol) were dissolved in benzene (12 mL) and refluxed for 3 h. The reaction mixture was diluted with EtOAc, and the organic phase was washed with aqueous saturated NaHCO3 (1×) and H2O (2×), dried over Na2SO4, and concentrated. Purification via silica gel chromatography using 0-5% EtOAc in CH2Cl2/hexanes (1:1) gave 6-bromo-4-chloro-2-(2-methoxyphenyl)quinazoline. LC/MS: m/z 348.9 (M+H)+ at 3.66 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. temperaturerefluxed for 3 h
  2. washthe organic phase was washed with aqueous saturated NaHCO3 (1×) and H2O (2×)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customPurification via silica gel chromatography

Sources & evidence

ORD record
ord-bc610a5237e8420b986884c2c6aeb877
Source dataset
uspto-grants-2011_04
Patent number
US07928107B2

Reaction notes

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