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

HRID 1384653Notes

Reaction equation

HRID 1384653 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>CO.[Pd]>[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. m.p. 205-210° C. 1H NMR Spectrum: (DMSOd6) 2.22(s, 3H); 3.85(s, 3H); 7.24(d, 1H); 7.35(dd, 1H); 7.42(d, 1H); 7.45(d, 1H); 8.58(d, 1H); 8.81(s, 1H); 11.40(s, 1H); 11.76(s, 1H) MS-ESI: 344 [MH]+

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-5a8b2ab286b34860bf956ccea7061600
Source dataset
uspto-grants-2001_07
Patent number
US06258951B1

Reaction notes

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