Methyl iodide → HCID 11174663, compound

HRID 1351192Notes

Reaction equation

HRID 1351192 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]=[CH:20][CH:19]=1)=[N:7][CH:8]=[N:9]2)[CH:2]=[CH2:3].[C:24]([O-])([O-])=O.[K+].[K+].CI>CC(C)=O>[CH2:1]([C:4]1[C:13]([O:14][CH3:24])=[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]=[CH:20][CH:19]=1)=[N:7][CH:8]=[N:9]2)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 21098393HCID 21098393, compound

Product 1

HCID 11174663HCID 11174663, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 5-allyl-7-methoxy-4-phenylamino-quinazolin-6-ol (0.16 g, 0.524 mmol) (from Example 15, Step D, supra) in acetone (30 mL) was added K2CO3 (0.36 g, 2.62 mmol) and methyl iodide (0.15 g, 1.05 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 (1:5:0.05) as eluent to give the desired (5-allyl-6,7-dimethoxy-quinazolin-4-yl)-phenyl-amine as a pale yellow solid. (Yield 0.13 g, 77%).

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-dae9a2ec8d2e499bbf204467a9e322e0
Source dataset
uspto-grants-2007_05
Patent number
US07217717B2

Reaction notes

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