1,2-Dibromoethane → 7-(2-Bromoethoxy)-6-methoxy4-phenoxyquinazoline

HRID 634702Notes

Reaction equation

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

Participants

Conditions

Temperature: 85 °C

Procedure

1,2-Dibromoethane (1.6 ml, 18.6 mmol) was added to 7-hydroxy-6-methoxy-4-phenoxyquinazoline (0.5 g, 1.86 mmol), (prepared as described for the starting material in Example 16), and potassium carbonate (1.2 g, 8.7 mmol) in DMF (60 ml) and the mixture was heated at 85° C. for 2 hours, and was then allowed to cool. The insolubles were removed by filtration, and the volatiles were removed from the filtrate by evaporation to give a residue which was purified by column chromatography eluting with methylene chloride/methanol (97/3) to give 7-(2-bromoethoxy)-6-methoxy-4-phenoxyquinazoline (440 mg, 63%).

Workup

custom(prepared
temperatureto cool
customThe insolubles were removed by filtration
customthe volatiles were removed from the filtrate by evaporation
customto give a residue which
customwas purified by column chromatography
washeluting with methylene chloride/methanol (97/3)

Sources & evidence

ORD record: ord-94cb4230daf0477eb055c21707096ad9
Source dataset: uspto-grants-2001_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06184225B2

Reaction notes

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