Potassium Hydroxide → HCID 10295513, compound

HRID 634624Notes

Reaction equation

HRID 634624 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=[C:10]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:9]=2)=[CH:3][CH:2]=1.[OH-].[K+].[CH3:26][O:27][C:28]1[CH:35]=[CH:34][C:31]([CH2:32]Cl)=[CH:30][CH:29]=1>CC(C)=O.C(OCC)(=O)C>[CH3:26][O:27][C:28]1[CH:35]=[CH:34][C:31]([CH2:32][N:7]([C:4]2[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=2)[C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[N:11]=[C:10]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:9]=2)=[CH:30][CH:29]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 699934-Methyloxybenzyl chlorideHCID 6456587HCID 6456587, compound

Product 1

HCID 10295513HCID 10295513, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-(4-pyridylamino)-2-phenyl quinazoline, 1 equivalent, was dissolved in reagent grade acetone, to this was added 5 equivalents of potassium hydroxide and 1.5 equivalents of 4-methoxybenzyl chloride. The mixture was refluxed under nitrogen for 4 hours. After cooling to room temperature the reaction mixture was concentrated and the residue taken up in ethyl acetate and washed with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate and concentrated to give an oil. This crude material was dissolved in ethyl acetate and chromatographed as in Example 1. EIMS confirmed the product.

Workup

  1. temperatureThe mixture was refluxed under nitrogen for 4 hours
  2. concentrationwas concentrated
  3. washwashed with saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customto give an oil
  7. customchromatographed as in Example 1

Sources & evidence

ORD record
ord-d9826b119ec949188d1d82f99cb9ae9a
Source dataset
uspto-grants-2001_02
Patent number
US06184226B2

Reaction notes

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