Toluene → HCID 22243815, compound

HRID 1597222Notes

Reaction equation

HRID 1597222 reaction equation
[N:1]1([CH2:6][CH2:7][O:8][C:9]2[NH:18][C:17](=O)[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.CN(C=O)C.C1(C)C=CC=CC=1>S(Cl)(Cl)=O>[N:1]1([CH2:6][CH2:7][O:8][C:9]2[N:18]=[CH:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 1140TolueneHCID 6228DimethylformamideHCID 136364241HCID 136364241, compound

Product 1

HCID 22243815HCID 22243815, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

A solution of 6-methoxy-7-(2-(pyrrolidin-1-yl)ethoxy-3,4-dihydroquinazolin-4-one (909 mg, 3.14 mmol) in thionyl chloride (12 ml) containing DMF (0.5 ml) was refluxed for I hour. After cooling toluene was added and the volatiles were removed by evaporation. The residue was partitioned between methylene chloride and water and the aqueous layer was adjusted to pH8 with sodium hydrogen carbonate. The organic layer was separated, washed with brine, dried (MgSO4), filtered and evaporated. The residue was purified by flash chromatography eluting with methylene chloride/methanol (95/5 followed by 85/15). The residue was triturated with ether, collected by filtration and dried under vacuum to give 4-chloro-6-methoxy-7-(2-(pyrrolidin-1-yl)ethoxyquinazoline (638 mg, 66%).

Workup

  1. temperaturewas refluxed for I hour
  2. additionwas added
  3. customthe volatiles were removed by evaporation
  4. customThe residue was partitioned between methylene chloride and water
  5. customThe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified by flash chromatography
  11. washeluting with methylene chloride/methanol (95/5 followed by 85/15)
  12. customThe residue was triturated with ether
  13. filtrationcollected by filtration
  14. customdried under vacuum

Sources & evidence

ORD record
ord-bfda0ead46ed42babaa21faf73dd6403
Source dataset
uspto-grants-2001_09
Patent number
US06294532B1

Reaction notes

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