7-Benzyloxy4-(4-bromo-2-fluoroanilino)-6-methoxyquinazoline hydrochloride → 4-[(4-Bromo-2-fluorophenyl)amino]-6-methoxy-7-quinazolinol

HRID 346544Notes

Reaction equation

HRID 346544 reaction equation
Cl.C([O:9][C:10]1[CH:19]=[C:18]2[C:13]([C:14]([NH:20][C:21]3[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][C:22]=3[F:28])=[N:15][CH:16]=[N:17]2)=[CH:12][C:11]=1[O:29][CH3:30])C1C=CC=CC=1>C(O)(C(F)(F)F)=O>[Br:27][C:24]1[CH:25]=[CH:26][C:21]([NH:20][C:14]2[C:13]3[C:18](=[CH:19][C:10]([OH:9])=[C:11]([O:29][CH3:30])[CH:12]=3)[N:17]=[CH:16][N:15]=2)=[C:22]([F:28])[CH:23]=1

Participants

3

Reactant 1

HCID 187534737-Benzyloxy4-(4-bromo-2-fluoroanilino)-6-methoxyquinazoline hydrochloride

Product 1

HCID 1355038524-[(4-Bromo-2-fluorophenyl)amino]-6-methoxy-7-quinazolinolYield 82%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 7-benzyloxy-4-(4-bromo-2-fluoroanilino)-6-methoxyquinazoline hydrochloride (9.4 g, 19.1 mmol) in TFA (90 ml) was heated at reflux for 50 minutes. The mixture was allowed to cool and was poured on to ice. The resulting precipitate was collected by filtration and dissolved in methanol (70 ml). The solution was adjusted to pH 9–10 with concentrated aqueous ammonia solution. The mixture was concentrated to half initial volume by evaporation. The resulting precipitate was collected by filtration, washed with water and then ether, and dried under vacuum to give 4-(4-bromo-2-fluoroanilino)-7-hydroxy-6-methoxyquinazoline (5.66 g, 82%).

Workup

  1. temperatureat reflux for 50 minutes
  2. temperatureto cool
  3. additionwas poured on to ice
  4. filtrationThe resulting precipitate was collected by filtration
  5. dissolutiondissolved in methanol (70 ml)
  6. concentrationThe mixture was concentrated to half initial volume
  7. customby evaporation
  8. filtrationThe resulting precipitate was collected by filtration
  9. washwashed with water
  10. dry with materialether, and dried under vacuum

Sources & evidence

ORD record
ord-6217dab6548548abb1d0bf20898ba21b
Source dataset
uspto-grants-2007_02
Patent number
US07173038B1

Reaction notes

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