Dimethylformamide → 4-Chloro-6-methoxy-7-(4-pyridylmethoxy)quinazoline

HRID 1386297Notes

Reaction equation

HRID 1386297 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][C:15]1[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=1)[N:9]=[CH:8][NH:7][C:6]2=O.CN(C=O)C.S(Cl)([Cl:29])=O>C1(C)C=CC=CC=1>[Cl:29][C:6]1[C:5]2[C:10](=[CH:11][C:12]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=[CH:8][N:7]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 135671184HCID 135671184, compound

Product 1

HCID 226249154-Chloro-6-methoxy-7-(4-pyridylmethoxy)quinazolineYield 55%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 6-methoxy-7-(4-pyridylmethoxy)-3,4-dihydroquinazolin-4-one (300 mg, 1.06 mmol) in thionyl chloride (5 ml) containing DMF (50 μl) was heated at reflux for 1 hour. The mixture was allowed to cool, diluted with toluene and the volatiles were removed by evaporation. The residue was dissolved in methylene chloride and a cooled solution of aqueous sodium hydrogen carbonate was added. The resulting precipitate was collected by filtration, washed with ether and dried under vacuum to give 4-chloro-6-methoxy-7-(4-pyridylmethoxy)quinazoline (175 mg, 55%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1 hour
  3. temperatureto cool
  4. customthe volatiles were removed by evaporation
  5. dissolutionThe residue was dissolved in methylene chloride
  6. additiona cooled solution of aqueous sodium hydrogen carbonate was added
  7. filtrationThe resulting precipitate was collected by filtration
  8. washwashed with ether
  9. customdried under vacuum

Sources & evidence

ORD record
ord-173ee748223e466bace5d9a1c1aa982d
Source dataset
uspto-grants-2001_07
Patent number
US06265411B1

Reaction notes

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