5-Amino-2,4-difluorophenol → 4-(2,4-Difluoro-5-hydroxyanilino)-6,7-dimethoxyquinazoline hydrochloride

HRID 634667Notes

Reaction equation

HRID 634667 reaction equation
Cl.[Cl:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:15][CH3:16])=[C:10]([O:13][CH3:14])[CH:11]=2)[N:6]=[CH:5][N:4]=1.[F:17][C:18]1[CH:24]=[C:23]([F:25])[C:22]([OH:26])=[CH:21][C:19]=1[NH2:20]>C(O)(C)C>[ClH:2].[F:17][C:18]1[CH:24]=[C:23]([F:25])[C:22]([OH:26])=[CH:21][C:19]=1[NH:20][C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:15][CH3:16])=[C:10]([O:13][CH3:14])[CH:11]=2)[N:6]=[CH:5][N:4]=1

Participants

4

Reactant 2

HCID 27829995-Amino-2,4-difluorophenolHCID 220221614-Chloro-6,7-dimethoxyquinazoline hydrochloride

Product 1

HCID 212603204-(2,4-Difluoro-5-hydroxyanilino)-6,7-dimethoxyquinazoline hydrochlorideYield 75.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

4-Chloro-6,7-dimethoxyquinazoline hydrochloride (300 mg, 1.15 mmol), (prepared as described for the starting material in Example 1 but without the aqueous work up), and 2,4-difluoro-5-hydroxyaniline (184 mg, 0.90 mmol) in isopropanol (10 ml) were heated at reflux for 2 hours. The reaction mixture was then allowed to cool, the precipitated product collected by filtration, washed with isopropanol and dried to give 4-(2,4-difluoro-5-hydroxyanilino)-6,7-dimethoxyquinazoline hydrochloride (250 mg, 65%)

Workup

  1. temperaturewere heated
  2. temperatureat reflux for 2 hours
  3. temperatureto cool
  4. filtrationthe precipitated product collected by filtration
  5. washwashed with isopropanol
  6. customdried

Sources & evidence

ORD record
ord-87eca4622cfc4c3b9729c4d1e2387531
Source dataset
uspto-grants-2001_02
Patent number
US06184225B2

Reaction notes

Loading…