Phosphorus oxychloride → 7-Bromo-4-chloro-2-methoxyquinazoline

HRID 1473664Notes

Reaction equation

HRID 1473664 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=O)[NH:7][C:8]([O:12][CH3:13])=[N:9]2)=[CH:4][CH:3]=1.C1CCN2C(=NCCC2)CC1.O=P(Cl)(Cl)[Cl:28]>C(Cl)Cl>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([Cl:28])=[N:7][C:8]([O:12][CH3:13])=[N:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 1364090737-bromo-2-methoxyquinazolin-4(3H)-one

Product 1

HCID 866877407-Bromo-4-chloro-2-methoxyquinazoline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 7-bromo-2-methoxyquinazolin-4(3H)-one (1.900 g, 7.45 mmol) in 30 mL DCM was treated with DBU (1.123 ml, 7.45 mmol) and was allowed to stir for 20 minutes. The cloudy purple solution was then treated with POCl3 (0.833 ml, 8.94 mmol) and was allowed to stir for one hour at room temperature. LC/MS showed mostly product, so the reaction mixture was concentrated. The crude residue was carried on to step 3 without purification. (M+H)+=271.2.

Workup

  1. stirringto stir for one hour at room temperature
  2. concentrationso the reaction mixture was concentrated
  3. customThe crude residue was carried on to step 3 without purification

Sources & evidence

ORD record
ord-9393c27266bf4fdba58db712976346a9
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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