Hydrochloric Acid → HCID 21260315, compound

HRID 634679Notes

Reaction equation

[CH2:1]([O:8][C:9]1[C:10]([CH3:30])=[CH:11][C:12]([F:29])=[C:13]([CH:28]=1)[NH:14][C:15]1[C:24]2[C:19](=[CH:20][C:21]([OH:27])=[C:22]([O:25][CH3:26])[CH:23]=2)[N:18]=[CH:17][N:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:32][CH2:33][OH:34].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C=O)C.O>[CH2:1]([O:8][C:9]1[C:10]([CH3:30])=[CH:11][C:12]([F:29])=[C:13]([CH:28]=1)[NH:14][C:15]1[C:24]2[C:19](=[CH:20][C:21]([O:27][CH2:32][CH2:33][OH:34])=[C:22]([O:25][CH3:26])[CH:23]=2)[N:18]=[CH:17][N:16]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 4-(5-benzyloxy-2-fluoro4-methylanilino)-7-hydroxy-6-methoxyquinazoline (440 mg, 1 mmol), 2-bromoethanol (77 ml, 1 mmol) and potassium carbonate (150 mg, 1.1 mmol) in DMF (5 ml) was heated at 50° C. for 1 hour, further 2-bromoethanol (42 ml, 0.6 mmol) and potassium carbonate (150 mg, 1.1 mmol) was added and the mixture was maintained at 50° C. for 2 hours. The reaction mixture was diluted with water, neutralised with 2M hydrochloric acid and extracted with ethyl acetate. The extracts were dried (MgSO4), the solvent removed by evaporation and the residue triturated with ether and hexane to give 4-(5-benzyloxy-2-fluoro-4-methylanilino)-7-(2-hydroxyethoxy)-6-methoxyquinazoline (200 mg, 41%).

Workup

temperaturethe mixture was maintained at 50° C. for 2 hours
extractionextracted with ethyl acetate
dry with materialThe extracts were dried (MgSO4)
customthe solvent removed by evaporation
customthe residue triturated with ether and hexane

Sources & evidence

ORD record: ord-391cc5780fbb44a09f589090779d4f2f
Source dataset: uspto-grants-2001_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06184225B2

Reaction notes

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