Chloroform → 4-(2-Fluoro-5-methoxycarbonyloxy-4-methylanilino)-7-hydroxyquinazoline hydrochloride

HRID 1421033Notes

Reaction equation

HRID 1421033 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]=[C:25]([O:27][C:28]([O:30][CH3:31])=[O:29])[C:24]([CH3:32])=[CH:23][C:22]=3[F:33])=[N:15][CH:16]=[N:17]2)=[CH:12][CH:11]=1)C1C=CC=CC=1.CN(C=O)C.[Cl:39]C(Cl)Cl>[Pd].CO>[ClH:39].[F:33][C:22]1[CH:23]=[C:24]([CH3:32])[C:25]([O:27][C:28]([O:30][CH3:31])=[O:29])=[CH:26][C:21]=1[NH:20][C:14]1[C:13]2[C:18](=[CH:19][C:10]([OH:9])=[CH:11][CH:12]=2)[N:17]=[CH:16][N:15]=1

Participants

6

Reactant 3

HCID 6212ChloroformHCID 6228DimethylformamideHCID 226249607-Benzyloxy-4-(2-fluoro-5-methoxycarbonyloxy-4-methylanilino)quinazoline hydrochloride

Product 1

HCID 1356711774-(2-Fluoro-5-methoxycarbonyloxy-4-methylanilino)-7-hydroxyquinazoline hydrochlorideYield 84%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

7-Benzyloxy-4-(2-fluoro-5-methoxycarbonyloxy-4-methylanilino)quinazoline hydrochloride (1.53 g, 3.25 mmol) and 10% palladium-on-charcoal catalyst (180 mg) in a mixture of methanol (75 ml), DMF (6 ml) and trichloromethane (30 ml) was stirred under hydrogen at 1.5 atmospheres pressure for 45 minutes. The catalyst was removed by filtration through diatomaceous earth and the solvent removed from the filtrate by evaporation. The residue was triturated with ether, the resulting solid was collected by filtration and dried under vacuum to give 4-(2-fluoro-5-methoxycarbonyloxy-4-methylanilino)-7-hydroxyquinazoline hydrochloride (1.23 g, 84%) as an orange solid.

Workup

  1. customThe catalyst was removed by filtration through diatomaceous earth
  2. customthe solvent removed from the filtrate by evaporation
  3. customThe residue was triturated with ether
  4. filtrationthe resulting solid was collected by filtration
  5. customdried under vacuum

Sources & evidence

ORD record
ord-f41897c038f4487f91d05e1c581d0d1b
Source dataset
uspto-grants-2000_06
Patent number
US06071921

Reaction notes

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