Phosphorus oxychloride → 4-Chloro-5-methylquinazoline

HRID 900313Notes

Reaction equation

HRID 900313 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4](=O)[NH:5][CH:6]=[N:7]2.O=P(Cl)(Cl)[Cl:15]>C1(C)C=CC=CC=1>[Cl:15][C:4]1[C:3]2[C:8](=[CH:9][CH:10]=[CH:11][C:2]=2[CH3:1])[N:7]=[CH:6][N:5]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1354187585-Methyl-4-quinazolone

Product 1

HCID 134955764-Chloro-5-methylquinazolineYield 85%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 1A (1.44 g, 9.0 mmol) in toluene (24 ml) was added POCl3 (13.5 ml) and DEA (3.6 ml). The mixture was refluxed under N2 for 30 min. After cooling to room temperature, the reaction mixture was concentrated under vacuum. The residue was dissolved in EtOAc, washed with 10% citric acid solution, followed by saturated NaHCO3. The residue was dried with MgSO4, filtered, and concentrated to give 1B (1.37 g, 85%) as a solid. 1H-NMR (400 MHz, CDCl3): 8.96 (s, 1H), 7.94 (d, J=8.52 Hz, 1H), 7.80 (dd, J=7.17 Hz, J=8.52 Hz, 1H), 7.51 (d, J=7.17 Hz, 1H), 3.05 (s, 3H).

Workup

  1. temperatureThe mixture was refluxed under N2 for 30 min
  2. concentrationthe reaction mixture was concentrated under vacuum
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with 10% citric acid solution
  5. dry with materialThe residue was dried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5b0725cb51074f93987b1d157a5d92f7
Source dataset
uspto-grants-2008_04
Patent number
US07358256B2

Reaction notes

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