2,6-Lutidine → 7-Bromo-4-chloro-2-(chloromethyl)quinazoline

HRID 968604Notes

Reaction equation

HRID 968604 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=O)[NH:7][C:8]([CH2:12][Cl:13])=[N:9]2)=[CH:4][CH:3]=1.N1C(C)=CC=CC=1C.P(Cl)(Cl)([Cl:25])=O>COCCOC>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([Cl:25])=[N:7][C:8]([CH2:12][Cl:13])=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 24813Phosphorus oxychlorideHCID 1356820607-Bromo-2-(chloromethyl)quinazolin-4-ol

Product 1

HCID 220301087-Bromo-4-chloro-2-(chloromethyl)quinazoline

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

Heat a mixture of 7-bromo-2-chloromethyl-3H-quinazolin-4-one (5 g, 18.2 mmol), 2,6-lutidine (5 g), and phosphorus oxychloride (5 mL) in 1,2-dimethoxyethane (500 mL) at 80° C. for 16 hours. Cool the mixture to room temperature and fully evaporate the mixture, then dilute with ether and wash with water. Dry the solvent (Na2SO4) and evaporate the ether to obtain 7-bromo-4-chloro-2-chloromethylquinazoline (3.5 g) as a yellow solid.

Workup

  1. temperatureHeat
  2. customfully evaporate the mixture
  3. additiondilute with ether
  4. washwash with water
  5. dry with materialDry the solvent (Na2SO4)
  6. customevaporate the ether

Sources & evidence

ORD record
ord-841955b274844056ab2b59676c656c06
Source dataset
uspto-grants-2007_12
Patent number
US07304059B2

Reaction notes

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