Hexane → 4-(4-Chloro-2,6-difluoroanilino)-6,7-dimethoxyquinazoline hydrochloride

HRID 634682Notes

Reaction equation

HRID 634682 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.Cl.[Cl:18][C:19]1[CH:25]=[C:24]([F:26])[C:22]([NH2:23])=[C:21]([F:27])[CH:20]=1.CCCCCC>C(O)(C)C>[ClH:2].[Cl:18][C:19]1[CH:25]=[C:24]([F:26])[C:22]([NH:23][C:3]2[C:12]3[C:7](=[CH:8][C:9]([O:15][CH3:16])=[C:10]([O:13][CH3:14])[CH:11]=3)[N:6]=[CH:5][N:4]=2)=[C:21]([F:27])[CH:20]=1

Participants

5

Reactant 3

HCID 8058HexaneHCID 212602804-Chloro-2,6-difluoroaniline hydrochlorideHCID 220221614-Chloro-6,7-dimethoxyquinazoline hydrochloride

Product 1

HCID 212603464-(4-Chloro-2,6-difluoroanilino)-6,7-dimethoxyquinazoline hydrochlorideYield 16%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

4-Chloro-6,7-dimethoxyquinazoline hydrochloride (210 mg, 0.8 mmol), (prepared as described for the starting material in Example 1 but without the aqueous work up), and 4-chloro-2,6-difluoroaniline hydrochloride (177 mg, 0.89 mmol) in isopropanol (8 ml) were heated at reflux for 2 hours. The reaction mixture was then allowed to cool, hexane added and the precipitated product collected by filtration, washed with isopropanol and dried to give 4-(4-chloro-2,6-difluoroanilino)-6,7-dimethoxyquinazoline hydrochloride (45 mg, 16%).

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-1c08663b789746239cd3db8c214771a6
Source dataset
uspto-grants-2001_02
Patent number
US06184225B2

Reaction notes

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