Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | Bis(2-bromoethyl) ether | HCID 21521 | — |
| Reactant | 4-(4-Chloro-2-fluorophenylamino)-7-hydroxy-6-methoxyquinazoline | HCID 135513720 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 594801 | HCID 594801 | 153.7% |
Reaction Steps
2-Bromoethyl ether (1.57 ml, 12 mmol) was added to a mixture of 4-(4-chloro-2-fluoroanilino)-7-hydroxy-6-methoxyquinazoline (1 g, 3.1 mmol), (prepared as described for the starting material in Example, 2), and potassium carbonate (1.73 g, 12 mmol) in DMF (10 ml). The mixture was stirred for 18 hours at ambient temperature and was partitioned between ethyl acetate and water. The organic layer was separated, washed with water and then brine, dried (MgSO4) and the solvent removed by evaporation. The residue was purified by column chromatography on silica eluting with methylene chloride/acetonitrile/methanol (60/38/2). The purified product was triturated with ether, collected by filtration, washed with ether and dried under vacuum to give 7-(22-bromoethoxy)ethoxy)-4-(4-chloro-2-fuoroanilino) methoxyquinazoline (763 mg, 52%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06897210B2 |
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| Source dataset | uspto-grants-2005_05 |
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| ORD ID | ord-2cbd05f8e1544970a59f1da976dd12ab |
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| Source note | uspto-grants-2005_05 |
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