Water → 6,7-Dimethoxyquinazoline

HRID 2213854Notes

Reaction equation

HRID 2213854 reaction equation
IC1C=CC(O[C:7]2[C:16]3[C:11](=[CH:12][C:13]([O:19][CH3:20])=[C:14]([O:17][CH3:18])[CH:15]=3)[N:10]=[CH:9][N:8]=2)=CC=1.C(OCC)(=O)C=C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.O>C(N(CC)CC)C.C(#N)C.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:18][O:17][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][C:13]=1[O:19][CH3:20])[N:10]=[CH:9][N:8]=[CH:7]2

Participants

9

Reactant 4

HCID 962WaterHCID 8821Ethyl AcrylateHCID 80271Tri-o-tolylphosphineHCID 219588884-(4-Iodophenoxy)-6,7-dimethoxyquinazoline

Product 1

HCID 30316616,7-DimethoxyquinazolineYield 136.7%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

Palladium (II) acetate (11 mg, 0.05 mmol) was added to a solution of 4-(4-iodophenoxy)-6,7-dimethoxyquinazoline (205 mg, 0.50 mmol), ethyl acrylate (50 mg, 0.50 mmol) and tri(o-tolyl)phosphine (30 mg, 0.10 mmol) in a mixture of triethylamine (3 ml) and acetonitrile (9 ml) and the reaction heated at reflux for 16 hours under an inert atmosphere. The reaction was cooled to ambient temperature, poured into water (30 ml), diluted with ethyl acetate (25 ml) and filtered through celite. The organic layer was separated, the aqueous was extracted with ethyl acetate (2×25 ml) and the combined organic layers were dried over magnesium sulphate before solvent evaporation in vacuo. Purification by flash chromatography on silica gel, eluting with ethyl acetate/isohexane (1:1), yielded 4-(4-(2-carboethoxy)ethenyl)phenoxy)-6,7-dimethoxyquinazoline (130 mg, 68% yield) as a cream solid:

Workup

  1. temperaturethe reaction heated
  2. temperatureat reflux for 16 hours under an inert atmosphere
  3. filtrationfiltered through celite
  4. customThe organic layer was separated
  5. extractionthe aqueous was extracted with ethyl acetate (2×25 ml)
  6. dry with materialthe combined organic layers were dried over magnesium sulphate before solvent evaporation in vacuo
  7. customPurification by flash chromatography on silica gel
  8. washeluting with ethyl acetate/isohexane (1:1)

Sources & evidence

ORD record
ord-48ef13b6c11b4a2ab07535f278af9cd3
Source dataset
uspto-grants-2006_09
Patent number
US07105669B1

Reaction notes

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