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

HRID 1351206
Notes
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Reaction equation

HRID 1351206 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][CH:21]=[C:20]([Br:24])[CH:19]=1)=[N:7][CH:8]=[N:9]2)[CH:2]=[CH2:3].[C:25]([O-])([O-])=O.[K+].[K+].CI>CC(C)=O>[CH2:1]([C:4]1[C:13]([O:14][CH3:25])=[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][CH:21]=[C:20]([Br:24])[CH:19]=1)=[N:7][CH:8]=[N:9]2)[CH:2]=[CH2:3]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 112691685-Allyl-4-(3-bromo-phenylamino)-7-methoxy-quinazolin-6-ol

Product 1

HCID 11177044(5-Allyl-6,7-dimethoxy-quinazolin-4-yl)-(3-bromo-phenyl)-amine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 5-allyl-4-(3-bromo-phenylamino)-7-methoxy-quinazolin-6-ol (0.27 g, 0.7 mmol) (from Example 17, Step D, supra) in acetone (30 mL) was added K2CO3 (0.48 g, 3.5 mmol) and methyl iodide (0.4 g, 2.8 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 (1:3:0.01) as eluent to give the desired (5-allyl-6,7-dimethoxy-quinazolin-4-yl)-(3-bromo-phenyl)-amine as a yellow solid. (Yield 0.14 g, 50%).

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-695942dd518c4205a7eb585579d30537
Source dataset
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07217717B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes