Cesium carbonate → 2,8-Dichloro-6-(3,5-dimethoxyphenyl)quinazoline

HRID 56452Notes

Reaction equation

HRID 56452 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[N:8]=[C:7]([Cl:13])[N:6]=[CH:5]2.[CH3:14][O:15][C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[C:20]([O:22][CH3:23])[CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:13][C:7]1[N:6]=[CH:5][C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=[C:2]([C:18]3[CH:17]=[C:16]([O:15][CH3:14])[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=3)[CH:3]=2)[N:8]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 4374257(3,5-Dimethoxyphenyl)boronic acidHCID 59199294HCID 59199294, compound

Product 1

HCID 1180361742,8-Dichloro-6-(3,5-dimethoxyphenyl)quinazolineYield 41.2%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 6-bromo-2,8-dichloroquinazoline (4.0 g, 14.5 mmol), 3,5-dimethoxyphenylboronic acid (4.23 g, 16.0 mmol), cesium carbonate (9.42 g, 29.0 mmol) and Pd(PPh3)2Cl2 (220 mg, 0.70 mmol) in THF (200 mL) and water (10 mL) was degassed with nitrogen three times, and stirred at 80° C. for 5 hours. The reaction mixture was cooled to room temperature, directly concentrated and purified by silica gel chromatography (petroleum ether: dichloromethane=2:1˜1:1) to get the title compound as a yellow solid (2.0 g, 41%). MS (ES+) C16H12Cl2N2O2 requires: 334, 336, found: 335, 337 [M+H]+.

Workup

  1. customwas degassed with nitrogen three times
  2. temperatureThe reaction mixture was cooled to room temperature
  3. concentrationdirectly concentrated
  4. custompurified by silica gel chromatography (petroleum ether: dichloromethane=2:1˜1:1)

Sources & evidence

ORD record
ord-b6cf8aadc9494aa89770cc412d30f3d1
Source dataset
uspto-grants-2016_09
Patent number
US09434700B2

Reaction notes

Loading…