HCID 21260315, compound → HCID 21260302, compound

HRID 634681Notes

Reaction equation

HRID 634681 reaction equation
C([O:8][C:9]1[C:10]([CH3:33])=[CH:11][C:12]([F:32])=[C:13]([CH:31]=1)[NH:14][C:15]1[C:24]2[C:19](=[CH:20][C:21]([O:27][CH2:28][CH2:29][OH:30])=[C:22]([O:25][CH3:26])[CH:23]=2)[N:18]=[CH:17][N:16]=1)C1C=CC=CC=1.[H][H]>[Pd].C(OCC)(=O)C>[F:32][C:12]1[CH:11]=[C:10]([CH3:33])[C:9]([OH:8])=[CH:31][C:13]=1[NH:14][C:15]1[C:24]2[C:19](=[CH:20][C:21]([O:27][CH2:28][CH2:29][OH:30])=[C:22]([O:25][CH3:26])[CH:23]=2)[N:18]=[CH:17][N:16]=1

Participants

5

Reactant 2

HCID 21260315HCID 21260315, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21260302HCID 21260302, compoundYield 42.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-(5-benzyloxy-2-fluoro-4-methylanilino)-7-(2-hydroxyethoxy)-6-methoxyquinazoline (150 mg, 0.33 mmol), (prepared as described for the starting material in Example 13), and 10% palladium-on-charcoal catalyst (20 mg) in ethyl acetate (8 ml) was stirred under 1 atmosphere of hydrogen at ambient temperature for 18 hours. The catalyst was removed by filtration through diatomaceous earth and most of the solvent removed by evaporation and hexane added to the residue. The resulting precipitate was collected by filtration and dried to give 4-(2-fluoro-5-hydroxy-4-methylanilino)-7-(2-hydroxyethoxy)-6-methoxyquinazoline (50 mg, 41%).

Workup

  1. custom(prepared
  2. customThe catalyst was removed by filtration through diatomaceous earth and most of the solvent
  3. customremoved by evaporation and hexane
  4. additionadded to the residue
  5. filtrationThe resulting precipitate was collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-58c479c0fd72495fa7a7b431b9a07cbd
Source dataset
uspto-grants-2001_02
Patent number
US06184225B2

Reaction notes

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