Phosphorus oxychloride → 7-(Benzyloxy)-4-chloro-6-fluoroquinazoline

HRID 639985Notes

Reaction equation

HRID 639985 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](=O)[N:14]=[CH:15][NH:16]2)=[CH:11][C:10]=1[F:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)([Cl:23])=O>>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([Cl:23])=[N:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[F:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178518222HCID 178518222, compound

Product 1

HCID 866052297-(Benzyloxy)-4-chloro-6-fluoroquinazolineYield 71%

Procedure

7-(Benzyloxy)-6-fluoroquinazolin-4(1H)-one (2.00 g, 7.41 mmol) was taken up in phosphorus oxychloride (20 ml) and the reaction heated at reflux for 90 minutes. The reaction was cooled, azeotroped with toluene (2×50 ml) and taken up in dichloromethane (5 ml) The organic phase was washed with saturated aqueous sodium hydrogen carbonate solution and then dried over magnesium sulphate. Solvent evaporation in vacuo followed by drying of the solid in vacuo yielded 7-(benzyloxy)-4-chloro-6-fluoroquinazoline (1.50 g, 71% yield) as a pale yellow solid:

Workup

  1. temperaturethe reaction heated
  2. temperatureat reflux for 90 minutes
  3. temperatureThe reaction was cooled
  4. customazeotroped with toluene (2×50 ml)
  5. washwas washed with saturated aqueous sodium hydrogen carbonate solution
  6. dry with materialdried over magnesium sulphate
  7. customSolvent evaporation in vacuo
  8. customby drying of the solid in vacuo

Sources & evidence

ORD record
ord-ca03047da7584cbb8bc72527437c1f75
Source dataset
uspto-grants-2010_04
Patent number
US07691867B2

Reaction notes

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