Diisopropylethylamine → 6,7-Dimethoxy-4-(3-hydroxyphenylthio)quinazoline

HRID 634652Notes

Reaction equation

HRID 634652 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[OH:16][C:17]1[CH:18]=[C:19]([SH:23])[CH:20]=[CH:21][CH:22]=1.C(N(CC)C(C)C)(C)C>CN(C=O)C.O>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH3:15])[N:5]=[CH:4][N:3]=[C:2]2[S:23][C:19]1[CH:20]=[CH:21][CH:22]=[C:17]([OH:16])[CH:18]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 27366133-HydroxybenzenethiolHCID 27693644-Chloro-6,7-dimethoxyquinazoline

Product 1

HCID 212602926,7-Dimethoxy-4-(3-hydroxyphenylthio)quinazolineYield 93%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

4-Chloro-6,7-dimethoxyquinazoline (200 mg, 0.89 mmol), (prepared as described for the starting material in Example 1), was added to a solution of 3-hydroxybenzenethiol (168 mg, 1.3 mmol) and N,N-diisopropylethylamine (233 μl, 1.3 mmol) in DMF (5 ml). After heating at 40° C. for 10 minutes, the reaction mixture was allowed to cool, diluted with water, acidified to pH3 and the mixture extracted with ethyl acetate. The organic extract was washed with brine, dried (MgSO4) and the solvent removed by evaporation. The residue was recrystallised from a mixture of ethanol and ether to give 6,7-dimethoxy-4-(3-hydroxyphenylthio)quinazoline (259 mg, 93%) as a white solid.

Workup

  1. temperatureto cool
  2. extractionthe mixture extracted with ethyl acetate
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed by evaporation
  7. customThe residue was recrystallised from a mixture of ethanol and ether

Sources & evidence

ORD record
ord-ed7956a85b914770a44041b5afb078a6
Source dataset
uspto-grants-2001_02
Patent number
US06184225B2

Reaction notes

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