Dimethylformamide → 4-Chloro-6-methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)quinazoline

HRID 855711Notes

Reaction equation

HRID 855711 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][CH2:16][N:17]1[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]1)[N:9]=[CH:8][NH:7][C:6]2=O.CN(C=O)C.S(Cl)([Cl:32])=O>>[Cl:32][C:6]1[C:5]2[C:10](=[CH:11][C:12]([O:13][CH2:14][CH2:15][CH2:16][N:17]3[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]3)=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=[CH:8][N:7]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 1354581696-Methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)-3,4-dihydroquinazolin-4-one

Product 1

HCID 112450614-Chloro-6-methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)quinazoline

Procedure

A solution of 6-methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)-3,4-dihydroquinazolin-4-one (2.05 g, 6.2 mmol) in thionyl chloride (30 ml) containing DMF (500 μl) was heated at reflux for 30 minutes. After cooling, the volatiles were removed by evaporation. The residue was partitioned between methylene chloride and saturated aqueous sodium hydrogen carbonate and the aqueous layer was adjusted to pH8 with solid sodium hydrogen carbonate. The organic layer was washed with water, brine, dried (MgSO4) and the volatiles were removed by evaporation. The residue was triturated with ether, collected by filtration, washed with ether and dried under vacuum to give 4-chloro-6-methoxy-7-(3-(4-methylpiperazin-1-yl)propoxy)quinazoline (1.4 g, 65).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 30 minutes
  3. temperatureAfter cooling
  4. customthe volatiles were removed by evaporation
  5. customThe residue was partitioned between methylene chloride and saturated aqueous sodium hydrogen carbonate
  6. washThe organic layer was washed with water, brine
  7. dry with materialdried (MgSO4)
  8. customthe volatiles were removed by evaporation
  9. customThe residue was triturated with ether
  10. filtrationcollected by filtration
  11. washwashed with ether
  12. customdried under vacuum

Sources & evidence

ORD record
ord-b3ba8b5e67e54e01bb9b861cb2c77479
Source dataset
uspto-grants-2007_08
Patent number
US07262201B1

Reaction notes

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