7-Benzyloxy4-(2-methoxyethylsulphanyl)quinazoline → 7-Hydroxy-4-(2-methoxyethylsulphanyl)quinazoline

HRID 1597245Notes

Reaction equation

HRID 1597245 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([S:19][CH2:20][CH2:21][O:22][CH3:23])=[N:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1)C1C=CC=CC=1>C(O)(C(F)(F)F)=O>[OH:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([S:19][CH2:20][CH2:21][O:22][CH3:23])=[N:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1

Participants

3

Reactant 1

HCID 216992667-Benzyloxy4-(2-methoxyethylsulphanyl)quinazoline

Product 1

HCID 1357987517-Hydroxy-4-(2-methoxyethylsulphanyl)quinazolineYield 100.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 7-benzyloxy-4-(2-methoxyethylsulphanyl)quinazoline (8 g, 24.5 mmol) in TFA (80 ml) was refluxed for 5 hours. After cooling and removal of the volatiles by evaporation, the residue was triturated with water, collected by filtration, washed with water and then ethyl acetate. The residue was resuspended in methylene chloride, filtered, washed with petroleum ether and dried under vacuum to give 7-hydroxy-4-(2-methoxyethylsulphanyl)quinazoline (5.8 g, quant.).

Workup

  1. temperatureAfter cooling
  2. customremoval of the volatiles
  3. customby evaporation
  4. customthe residue was triturated with water
  5. filtrationcollected by filtration
  6. washwashed with water
  7. filtrationfiltered
  8. washwashed with petroleum ether
  9. customdried under vacuum

Sources & evidence

ORD record
ord-f15a852f84aa42e3a4e3f8483a3b7d9a
Source dataset
uspto-grants-2001_09
Patent number
US06294532B1

Reaction notes

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