Methyl iodide → 2,5-Dichloro-8-methoxyquinazoline

HRID 2079680Notes

Reaction equation

HRID 2079680 reaction equation
[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[C:4](=[C:5]([OH:13])[CH:6]=[CH:7][C:8]=2[Cl:12])[N:3]=1.IC.[C:16](=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[C:4](=[C:5]([O:13][CH3:16])[CH:6]=[CH:7][C:8]=2[Cl:12])[N:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 591992212,5-Dichloroquinazolin-8-ol

Product 1

HCID 866393242,5-Dichloro-8-methoxyquinazoline

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2,5-dichloroquinazolin-8-ol (1 eq) (See example 32 for synthesis) in DMF was added iodomethane (3 eq) and potassium carbonate (3 eq). The reaction mixture was stirred at room temperature for overnight. Diluted with ethyl acetate and washed with water and brine and dried over sodium sulfate. Filtered, evaporated and dried to provide product as a yellow solid in quantitative yield. ES/MS m/z 229.0 (MH+). Proceed for next step.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over sodium sulfate
  3. filtrationFiltered
  4. customevaporated
  5. customdried
  6. customto provide product as a yellow solid in quantitative yield

Sources & evidence

ORD record
ord-d8a9731cfcf247aabd6ccb73a1975476
Source dataset
uspto-grants-2011_04
Patent number
US07932262B2

Reaction notes

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