Dichloromethane → 4-Chloroquinazoline

HRID 1690000Notes

Reaction equation

HRID 1690000 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-7273271edb2f44b081ecf3247c57f742
Source dataset
uspto-grants-2012_04
Patent number
US08153642B2

Reaction notes

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