Methyl iodide → (5-Allyl-6,7-dimethoxy-quinazolin-4-yl)-(3-chloro-4-fluoro-phenyl)-amine

HRID 1351211Notes

Reaction equation

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

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 5-allyl-4-(3-chloro-4-fluoro-phenylamino)-7-methoxy-quinazolin-6-ol (0.59 g, 1.63 mmol) (from Example 18, Step D, supra) in acetone (175 mL) was added K2CO3 (0.68 g, 4.91 mmol) and methyl iodide (2.32 g, 16.4 mmol) (Aldrich). The reaction mixture was heated with stirring at 90° C. for 3 hours. The mixture was cooled to room temperature, filtered and the filtrate was concentrated. The residue was purified by chromatography using EtOAc/CH2Cl2/Et3N (1:3:0.01) as eluent to give the desired (5-allyl-6,7-dimethoxy-quinazolin-4-yl)-(3-chloro-4-fluoro-phenyl)-amine as an off white solid. (Yield 0.29 g, 48%).

Workup

temperatureThe reaction mixture was heated
temperatureThe mixture was cooled to room temperature
filtrationfiltered
concentrationthe filtrate was concentrated
customThe residue was purified by chromatography

Sources & evidence

ORD record: ord-d5988527161f45b59b49dd5d722a70bb
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07217717B2

Reaction notes

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