4-Aminopyridine → HCID 6456587, compound

HRID 651218Notes

Reaction equation

HRID 651218 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:3]=1.[NH2:18][C:19]1[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[N:22]1[CH:23]=[CH:24][C:19]([NH:18][C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=[C:4]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:3]=2)=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 17274-AminopyridineHCID 11430Potassium CarbonateHCID 809774-Chloro-2-phenylquinazoline

Product 1

HCID 6456587HCID 6456587, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Chloro-2-phenyl quinazoline, 1 equivalent, was treated with 1 equivalent 4-aminopyridine and 1 equivalent potassium carbonate in dimethylformamide (DMF), under reflux for 4 hours. The reaction mixture was cooled to room temperature and concentrated under vacuum to an oil. This crude material was dissolved in ethyl acetate and chromatographed using hexane:ethyl acetate:methanol 8:2:0.5 to obtain solid product. Electron impact mass spectroscopy (EIMS) gave a molecular ion corresponding to the calculated molecular weight of the title compound.

Workup

  1. temperatureunder reflux for 4 hours
  2. concentrationconcentrated under vacuum to an oil
  3. dissolutionThis crude material was dissolved in ethyl acetate
  4. customchromatographed
  5. customto obtain solid product

Sources & evidence

ORD record
ord-c458cb8685c14671adbba3460a47105e
Source dataset
uspto-grants-2001_08
Patent number
US06277989B1

Reaction notes

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