HCID 21260357, compound → 7-(2-Acetoxyethoxy)-4-(2-fluoro-5-hydroxy4-methylanilino)-6-methoxyquinazoline

HRID 634673Notes

Reaction equation

HRID 634673 reaction equation
[C:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[CH:17]=[C:16]2[C:11]([C:12]([NH:18][C:19]3[CH:24]=[C:23]([O:25]CC4C=CC=CC=4)[C:22]([CH3:33])=[CH:21][C:20]=3[F:34])=[N:13][CH:14]=[N:15]2)=[CH:10][C:9]=1[O:35][CH3:36])(=[O:3])[CH3:2].[H][H]>[Pd].C(OCC)(=O)C>[C:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[CH:17]=[C:16]2[C:11]([C:12]([NH:18][C:19]3[CH:24]=[C:23]([OH:25])[C:22]([CH3:33])=[CH:21][C:20]=3[F:34])=[N:13][CH:14]=[N:15]2)=[CH:10][C:9]=1[O:35][CH3:36])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 21260357HCID 21260357, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 212603387-(2-Acetoxyethoxy)-4-(2-fluoro-5-hydroxy4-methylanilino)-6-methoxyquinazolineYield 15%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 7-(2-acetoxyethoxy)-4-(5-benzyloxy-2-fluoro-4-methylanilino)-6-methoxyquinazoline (133 mg, 0.27 mmol) and 10% palladium-on-charcoal catalyst (50 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 precipitated product was collected by filtration and dried to give 7-(2-acetoxyethoxy)-4-(2-fluoro-5-hydroxy4-methylanilino)-6-methoxyquinazoline (16 mg, 15%).

Workup

  1. customThe catalyst was removed by filtration through diatomaceous earth and most of the solvent
  2. customremoved by evaporation and hexane
  3. additionadded to the residue
  4. customThe resulting precipitated product
  5. filtrationwas collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-c5990c89cade4267922285d9ed2bf45c
Source dataset
uspto-grants-2001_02
Patent number
US06184225B2

Reaction notes

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