Potassium Carbonate → HCID 59682924, compound

HRID 1668687Notes

Reaction equation

HRID 1668687 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][Cl:17])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.[CH3:18][C:19]1[NH:20][C:21]2[C:26]([C:27]=1[CH3:28])=[CH:25][C:24]([OH:29])=[CH:23][CH:22]=2.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:17][CH2:16][CH2:15][O:14][C:8]1[CH:7]=[C:6]2[C:11]([C:2]([O:29][C:24]3[CH:25]=[C:26]4[C:21](=[CH:22][CH:23]=3)[NH:20][C:19]([CH3:18])=[C:27]4[CH3:28])=[N:3][CH:4]=[N:5]2)=[CH:10][C:9]=1[O:12][CH3:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 220307882,3-Dimethyl-1H-indol-5-olHCID 596829074-Chloro-7-(2-chloroethoxy)-6-methoxyquinazoline

Product 1

HCID 59682924HCID 59682924, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4-chloro-7-(2-chloroethoxy)-6-methoxyquinazoline (5.0 g), prepared as described in Example 7, 2,3-dimethyl-5-hydroxyindole (3.5 g), (Arch. Pharm. 1972, 305, 159), and potassium carbonate (4.0 g) in DMF (70 ml) was stirred and heated at 90° C. for 3 hours. The mixture was filtrated and the solvent was removed by evaporation under vacuum. The residue was purified by column chromatography on silica using the solvent mixture dichloromethane/ethyl acetate/methanol (50/48/2). The solvent was evaporated under vacuum to give 7-(2-chloroethoxy)-4-[(2,3-dimethyl-1H-indol-5-yl)oxy]-6-methoxyquinazoline (4.9 g) as a beige solid.

Workup

  1. customprepared
  2. filtrationThe mixture was filtrated
  3. customthe solvent was removed by evaporation under vacuum
  4. customThe residue was purified by column chromatography on silica using the solvent mixture dichloromethane/ethyl acetate/methanol (50/48/2)
  5. customThe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-016b006052824f84aad5f41bb464fca2
Source dataset
uspto-grants-2011_08
Patent number
US07989460B2

Reaction notes

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