7-(Benzyloxy)-4-(methylsulfanyl)quinazoline → 7-Hydroxy4-methylsulphanylquinazoline

HRID 1597239Notes

Reaction equation

HRID 1597239 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([S:19][CH3:20])=[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][CH3:20])=[N:14][CH:15]=[N:16]2)=[CH:11][CH:10]=1

Participants

3

Reactant 1

HCID 226493097-(Benzyloxy)-4-(methylsulfanyl)quinazoline

Product 1

HCID 1356740197-Hydroxy4-methylsulphanylquinazolineYield 98.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 7-benzyloxy4-methylsulphanylquinazoline (3 g, 10.6 mmol) in TFA (30 ml) was heated at reflux for 5 hours. After cooling, the volatiles were removed by evaporation. The residue was suspended in water and solid sodium hydrogen carbonate was added until complete dissolution. After extraction with ether, the aqueous layer was acidified to pH2 with 2M hydrochloric acid. The precipitate was collected by filtration, washed with water, followed by ether and dried under vacuum to give 7-hydroxy4-methylsulphanylquinazoline (2 g, quant.).

Workup

  1. temperatureat reflux for 5 hours
  2. temperatureAfter cooling
  3. customthe volatiles were removed by evaporation
  4. additionsolid sodium hydrogen carbonate was added until complete dissolution
  5. extractionAfter extraction with ether
  6. filtrationThe precipitate was collected by filtration
  7. washwashed with water
  8. customdried under vacuum

Sources & evidence

ORD record
ord-3ba3122f918e4cd69a863aac08259482
Source dataset
uspto-grants-2001_09
Patent number
US06294532B1

Reaction notes

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