Toluene → 4-Chloro-6-methoxy-7-(2-(pyrrolidin-1-yl)ethoxy)quinazoline

HRID 1386309Notes

Reaction equation

HRID 1386309 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH2:14][CH2:15][N:16]1[CH2:20][CH2:19][CH2:18][CH2:17]1)[N:9]=[CH:8][NH:7][C:6]2=O.C1(C)C=CC=CC=1.S(Cl)([Cl:31])=O>CN(C=O)C>[Cl:31][C:6]1[C:5]2[C:10](=[CH:11][C:12]([O:13][CH2:14][CH2:15][N:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=[CH:8][N:7]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 1354756166-Methoxy-7-(2-(pyrrolidin-1-yl)ethoxy)-3,4-dihydroquinazolin-4-one

Product 1

HCID 109357264-Chloro-6-methoxy-7-(2-(pyrrolidin-1-yl)ethoxy)quinazolineYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6methoxy-7-(2-(pyrrolidin-1-yl)ethoxy)-3,4-dihydroquinazolin-4-one (228 mg, 7.9 mmol) in thionyl chloride (5 ml) and DMF (0.2 ml) was heated at reflux for 1 hour. Toluene was added and the volatiles were removed by evaporation. The residue was dissolved in methylene chloride and cooled aqueous sodium hydrogen carbonate solution was added. The organic layer was separated, washed with brine, dried (MgSO4) and the solvent removed by evaporation to give 4-chloro-6-methoxy-7-(2-(pyrrolidin-1-yl)ethoxy)quinazoline (200 mg, 82%).

Workup

  1. temperatureat reflux for 1 hour
  2. customthe volatiles were removed by evaporation
  3. dissolutionThe residue was dissolved in methylene chloride
  4. temperaturecooled aqueous sodium hydrogen carbonate solution
  5. additionwas added
  6. customThe organic layer was separated
  7. washwashed with brine
  8. dry with materialdried (MgSO4)
  9. customthe solvent removed by evaporation

Sources & evidence

ORD record
ord-1e66513aabc2414980965370fcb2a88d
Source dataset
uspto-grants-2001_07
Patent number
US06265411B1

Reaction notes

Loading…