Triethylamine → 6-Bromo-4-chloro-quinazoline

HRID 1626324Notes

Reaction equation

HRID 1626324 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][NH:6][C:5]2=O.O=P(Cl)(Cl)[Cl:15].CCN(CC)CC>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]=[C:5]2[Cl:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 1354449056-bromoquinazolin-4-ol

Product 1

HCID 167703106-Bromo-4-chloro-quinazolineYield 95%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Next, to a dioxane solution containing 6-bromo-3H-quinazolin-4-one (B, 15.0 g, 66.7 mmol, 1.0 equiv) is added POCl3 (20.0 mL, d=1.67, 33.4 g, 219 mmol, 3.3 equiv). Et3N (30.0 mL, d=0.726, 21.8 g, 215 mmol) is then added dropwise to the solution. The reaction mixture is heated at reflux for 12 h. The solution is cooled to room temperature and poured into an ice-water mixture. Then, the resultant precipitate is collected by filtration, washed with H2O (100 mL), and dried under vacuum to provide the desired 6-bromo-4-chloro-quinazoline (C, 15.4 g, 63.2 mmol) in 95% yield: ESI-MS m/z 243.0 (M+H)+.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 12 h
  3. filtrationThen, the resultant precipitate is collected by filtration
  4. washwashed with H2O (100 mL)
  5. customdried under vacuum

Sources & evidence

ORD record
ord-941dc9fa3296492a8da27050b50738c2
Source dataset
uspto-grants-2014_07
Patent number
US08785459B2

Reaction notes

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