7-Benzyloxy-4-(2-fluoro-4-methylanilino)-6-methoxyquinazoline hydrochloride → HCID 135537648, compound

HRID 577381Notes

Reaction equation

HRID 577381 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]([CH3:27])=[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>[F:28][C:22]1[CH:23]=[C:24]([CH3:27])[CH:25]=[CH:26][C:21]=1[NH:20][C:14]1[C:13]2[C:18](=[CH:19][C:10]([OH:9])=[C:11]([O:29][CH3:30])[CH:12]=2)[N:17]=[CH:16][N:15]=1

Participants

3

Reactant 1

HCID 179732207-Benzyloxy-4-(2-fluoro-4-methylanilino)-6-methoxyquinazoline hydrochloride

Product 1

HCID 135537648HCID 135537648, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 7-benzyloxy-4-(2-fluoro-4-methylanilino)-6-methoxyquinazoline hydrochloride (2 g, 4.7 mmol) in TFA (20 ml) was heated at 80° C. for 5 hours and stirred at ambient temperature overnight. The volatiles were removed under vacuum and the residue was suspended in water (50 ml). Solid sodium hydrogen carbonate was added until the pH was approximately 7. The precipitate was then collected by filtration, washed with water and dried under vacuum. The solid was purified by column chromatography eluting with methanol/methylene chloride (5/95). After removal of the solvent by evaporation, the solid was triturated with ether, collected by filtration, washed with ether and dried under vacuum to give 4-(2-fluoro-4-methylanilino)-7-hydroxy-6-methoxyquinazoline (1.04 g, 74%).

Workup

  1. customThe volatiles were removed under vacuum
  2. additionSolid sodium hydrogen carbonate was added until the pH was approximately 7
  3. filtrationThe precipitate was then collected by filtration
  4. washwashed with water
  5. customdried under vacuum
  6. customThe solid was purified by column chromatography
  7. washeluting with methanol/methylene chloride (5/95)
  8. customAfter removal of the solvent
  9. customby evaporation
  10. customthe solid was triturated with ether
  11. filtrationcollected by filtration
  12. washwashed with ether
  13. customdried under vacuum

Sources & evidence

ORD record
ord-7018ffbe994245ec8ed06af6d2a97f98
Source dataset
uspto-grants-2015_05
Patent number
US09040548B2

Reaction notes

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