7-Benzyloxy-4-(4-chloro-2-fluorophenylamino)-6-methoxyquinazoline hydrochloride → 4-(4-Chloro-2-fluorophenylamino)-7-hydroxy-6-methoxyquinazoline

HRID 547167Notes

Reaction equation

HRID 547167 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]([Cl: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>[Cl: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 224782657-Benzyloxy-4-(4-chloro-2-fluorophenylamino)-6-methoxyquinazoline hydrochloride

Product 1

HCID 1355137204-(4-Chloro-2-fluorophenylamino)-7-hydroxy-6-methoxyquinazolineYield 72%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 7-benzyloxy-4-(4-chloro-2-fluoroanilino)-6-methoxyquinazoline hydrochloride (892 mg, 2 mmol) in TFA (10 ml) was refluxed for 50 minutes. After cooling, the mixture was poured onto ice. The precipitate was collected by filtration, dissolved in methanol (10 ml) and basified to pH11 with aqueous ammonia. After concentration by evaporation, the solid product was collected by filtration, washed with water then ether and dried under vacuum to give 4-(4-chloro-2-fluoroanilino)-7-hydroxy-6-methoxyquinazoline as a yellow solid (460 mg, 72%). m.p. 141-143° C.

Workup

  1. temperatureAfter cooling
  2. additionthe mixture was poured onto ice
  3. filtrationThe precipitate was collected by filtration
  4. dissolutiondissolved in methanol (10 ml)
  5. concentrationAfter concentration
  6. customby evaporation
  7. filtrationthe solid product was collected by filtration
  8. washwashed with water
  9. dry with materialether and dried under vacuum

Sources & evidence

ORD record
ord-7f23b25026ea4ffbbf92fdcb9bbd6b6a
Source dataset
uspto-grants-2011_05
Patent number
USRE042353E1

Reaction notes

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