Potassium Carbonate → HCID 21260285, compound

HRID 634647Notes

Reaction equation

[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C:7]2[C:16]3[C:11](=[CH:12][C:13]([OH:19])=[C:14]([O:17][CH3:18])[CH:15]=3)[N:10]=[CH:9][N:8]=2)=[C:4]([F:22])[CH:3]=1.[CH3:23][O:24][CH2:25][CH2:26]Br.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C:7]2[C:16]3[C:11](=[CH:12][C:13]([O:19][CH2:26][CH2:25][O:24][CH3:23])=[C:14]([O:17][CH3:18])[CH:15]=3)[N:10]=[CH:9][N:8]=2)=[C:4]([F:22])[CH:3]=1

Participants

Conditions

Temperature: 180 °C

Procedure

A mixture of 4-(4-chloro-2-fluorophenoxy)-7-hydroxy-6-methoxyquinazoline (160 mg, 0.5 mmol), 2-bromoethyl methyl ether (83 mg, 0.6 mmol) and potassium carbonate (207 mg. 1.5 mmol) in DMF (3 ml) was heated at 180° C. for 45 minutes. The reaction mixture was allowed to cool, diluted with water and acidified to pH3.5. This aqueous mixture was extracted with ethyl acetate and the organic extract was washed with water and brine, dried (MgSO4) and the solvent removed by evaporation. The residue was purified by flash chromatography eluting with methylene chloride/ether (7/3) to give 4-(4-chloro-2-fluorophenoxy)-7-(2-methoxyethoxy)-6-methoxyquinazoline (130 mg, 68%).

Workup

temperatureto cool
extractionThis aqueous mixture was extracted with ethyl acetate
extractionthe organic extract
washwas washed with water and brine
dry with materialdried (MgSO4)
customthe solvent removed by evaporation
customThe residue was purified by flash chromatography
washeluting with methylene chloride/ether (7/3)

Sources & evidence

ORD record: ord-75d3b8e405a74065b4080acf6ff85b25
Source dataset: uspto-grants-2001_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06184225B2

Reaction notes

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