Potassium Carbonate → HCID 594801, compound

HRID 2182573Notes

Reaction equation

HRID 2182573 reaction equation
BrC[CH2:3][O:4][CH2:5]CBr.ClC1C=CC([NH:13][C:14]2[C:23]3[C:18](=[CH:19][C:20](O)=[C:21](OC)[CH:22]=3)[N:17]=CN=2)=C(F)C=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:5][O:4][C:3]1[N:13]=[CH:14][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 21521Bis(2-bromoethyl) etherHCID 1355137204-(4-Chloro-2-fluorophenylamino)-7-hydroxy-6-methoxyquinazoline

Product 1

HCID 594801HCID 594801, compoundYield 153.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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%).

Workup

  1. custom(prepared
  2. customwas partitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materialbrine, dried (MgSO4)
  6. customthe solvent removed by evaporation
  7. customThe residue was purified by column chromatography on silica eluting with methylene chloride/acetonitrile/methanol (60/38/2)
  8. customThe purified product was triturated with ether
  9. filtrationcollected by filtration
  10. washwashed with ether
  11. customdried under vacuum

Sources & evidence

ORD record
ord-2cbd05f8e1544970a59f1da976dd12ab
Source dataset
uspto-grants-2005_05
Patent number
US06897210B2

Reaction notes

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