Aniline → 6-Acetoxy-7-methoxy-4-phenylamino-quinazoline

HRID 1351189Notes

Reaction equation

[C:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH3:16])[N:11]=[CH:10][NH:9][C:8]2=[O:17])(=[O:3])[CH3:2].[NH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O=S(Cl)Cl.CN(C=O)C>[C:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH3:16])[N:11]=[CH:10][NH:9][C:8]2=[O:17])(=[O:3])[CH3:2].[C:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH3:16])[N:11]=[CH:10][N:9]=[C:8]2[NH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

6-Acetoxy-7-methoxy-quinazolin-4-one (RO0505111-000) was synthesized according to the literature procedure of Gibson, K. H. et al. Bioorganic & Medicinal Chemistry Letters, 1997, 7(21), 2723–2728. To a solution of 6-acetoxy-7-methoxy-quinazolin-4-one (RO0505111-000) (1.2 g, 5.13 mmol) in SOCl2 (30 mL) Aldrich) was added a few drops of DMF (0.1 mL). The reaction mixture was then heated with stirring at 100° C. for 3 hours. The solvents were evaporated and the residue was dried in vacuo. The residue was dissolved in 2-propanol (30 mL), then aniline (0.47 mL, 5.13 mmol) (Aldrich) was added. The reaction mixture was heated at 110° C. for 3 hours, then cooled to room temperature and filtered. The precipitate was collected and dried in vacuo to give 6-acetoxy-7-methoxy-4-phenylamino-quinazoline as a white solid. (Yield 1.0 g, 63%).

Workup

temperatureThe reaction mixture was then heated
customThe solvents were evaporated
customthe residue was dried in vacuo
dissolutionThe residue was dissolved in 2-propanol (30 mL)
temperatureThe reaction mixture was heated at 110° C. for 3 hours
temperaturecooled to room temperature
filtrationfiltered
customThe precipitate was collected
customdried in vacuo

Sources & evidence

ORD record: ord-c775da01db5c4a399561b53a162d2c0c
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07217717B2

Reaction notes

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