Allyl bromide → (6-Allyloxy-7-methoxy-quinazolin-4-yl)-(3-chloro-4-fluoro-phenyl)-amine

HRID 1351209Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:21][CH3:22])=[C:17]([OH:20])[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[F:8].C([O-])([O-])=O.[K+].[K+].[CH2:29](Br)[CH:30]=[CH2:31]>CC(C)=O>[CH2:31]([O:20][C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][C:16]=1[O:21][CH3:22])[N:13]=[CH:12][N:11]=[C:10]2[NH:9][C:4]1[CH:5]=[CH:6][C:7]([F:8])=[C:2]([Cl:1])[CH:3]=1)[CH:30]=[CH2:29]

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 4-(3-chloro-4-fluoro-phenylamino)-7-methoxy-quinazolin-6-ol (0.70 g, 2.18 mmol) (from Example 18, Step B, supra) in acetone (140 mL) was added K2CO3 (0.61 g, 10.9 mmol) and allyl bromide (0.94 mL, 10.9 mmol) (Aldrich). The reaction mixture was heated with stirring at 90° C. for 4 hours. The mixture was cooled to room temperature, filtered, and the filtrate was concentrated. The residue was purified by chromatography using EtOAc/CH2C2/Et3N (1:1:0.02) as eluent to give the desired (6-allyloxy-7-methoxy-quinazolin-4-yl)-(3-chloro-4-fluoro-phenyl)-amine as an off white solid. (Yield 0.64 g, 82%).

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-c497aa9919e8410eae3113c6e13001a9
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07217717B2

Reaction notes

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