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

HRID 1791249Notes

Reaction equation

HRID 1791249 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-d14c368a73f7413183370a1f21e7e743
Source dataset
uspto-grants-2006_07
Patent number
US07074799B2

Reaction notes

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