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

HRID 1351197Notes

Reaction equation

HRID 1351197 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:20][CH3:21])=[C:16]([OH:19])[CH:17]=3)[N:12]=[CH:11][N:10]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH2:28](Br)[CH:29]=[CH2:30]>CC(C)=O>[CH2:30]([O:19][C:16]1[CH:17]=[C:18]2[C:13](=[CH:14][C:15]=1[O:20][CH3:21])[N:12]=[CH:11][N:10]=[C:9]2[NH:8][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)[CH:29]=[CH2:28]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 21098391HCID 21098391, compound

Product 1

HCID 21098403(6-Allyloxy-7-methoxy-quinazolin-4-yl)-(4-chloro-phenyl)-amine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 4-(4-chloro-phenylamino)-7-methoxy-quinazolin-6-ol (0.61 g, 2.02 mmol) (from Example 16, Step B, supra) in acetone (50 mL) was added K2CO3 (0.84 g, 6.06 mmol), and allyl bromide (0.52 mL, 6.06 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/CH2Cl2/Et3N (1:1:0.01) as eluent to give the desired (6-allyloxy-7-methoxy-quinazolin-4-yl)-(4-chloro-phenyl)-amine as a white solid. (Yield 0.5 g, 72%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-b8931bdca4ac4256b149d32004b06909
Source dataset
uspto-grants-2007_05
Patent number
US07217717B2

Reaction notes

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