Dichloromethane → 4-Chloroquinazoline

HRID 2244106Notes

Reaction equation

HRID 2244106 reaction equation
[CH:1]1[CH:2]=[CH:3][C:4]2[N:11]=[CH:10][NH:9][C:7](=O)[C:5]=2[CH:6]=1.C[Si](Br)(C)C.C(Cl)[Cl:18]>>[Cl:18][C:7]1[C:5]2[C:4](=[CH:3][CH:2]=[CH:1][CH:6]=2)[N:11]=[CH:10][N:9]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 76113BromotrimethylsilaneHCID 1354087534(1H)-Quinazolinone

Product 1

HCID 788644-ChloroquinazolineYield 100%

Conditions

Temperature
0 °C

Procedure

To a solution of the quinazoline 2 (0.168 g, 0.29 mmol) in DCM (1.5 mL) was added TMSBr (0.079 mL, 0.61 mmol) at 0° C. The reaction was stirred for 1 h at 0° C., then for 1 h at RT. The reaction was quenched with water (3 mL) and stirred for 15 min. The aqueous layer was washed with EtOAc (5 mL), and dried with lyophilizer overnight to give desired product 3 as white foam (0.14 g, 100% yield). LC/MS (10-99%) M/Z 406.0 retention time 3.32 min.

Workup

  1. waitfor 1 h at RT
  2. customThe reaction was quenched with water (3 mL)
  3. stirringstirred for 15 min
  4. washThe aqueous layer was washed with EtOAc (5 mL)
  5. customdried with lyophilizer overnight

Sources & evidence

ORD record
ord-ae542ff02089403d8a30dc15affd7308
Source dataset
uspto-grants-2010_03
Patent number
US07678802B2

Reaction notes

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