Reaction #722378

Reaction equation

compound

2-(2-n-Propoxyphenyl)-8-Iodoquinazolin-4(3H)-One

tributylamine

1-heptene

tri-o-tolylphosphine

→

2-(2-n-Propoxyphenyl)-8-(1-Hepten-1-yl)Quinazolin-4(3H)-One

Solvents

ethyl acetate

DMF

Conditions

Workup

1. 1
   Washthe mixture is washed 3 times with 50-ml portions of H2O
2. 2
   DryingAfter drying over MgSO4
3. 3
   Otherthe organic phase is evaporated under vacuum
4. 4
   Otherthe residue is chromatographed on silica gel with toluene/ethyl acetate 95:5 as eluant
5. 5
   workup.ADDITIONThe fractions containing the product
6. 6
   Otherthe solvent is evaporated under vacuum
7. 7
   OtherThe initially oily residue is crystallized

Procedure

5 g (12.31 mmoles) of the compound from Example III, 3.7 ml (15.4 mmoles) of tributylamine, 6.6 ml (46.2 mmoles) of 1-heptene, 375 mg of tri-o-tolylphosphine (1.23 mmoles), and 138 mg of palladium(II) acetate (0.6 mmole) are stirred in 50 ml of dry DMF for 2.5 h at 100° C. The mixture is cooled to room temperature, 50 ml of ethyl acetate is added, and the mixture is washed 3 times with 50-ml portions of H2O. After drying over MgSO4, the organic phase is evaporated under vacuum, and the residue is chromatographed on silica gel with toluene/ethyl acetate 95:5 as eluant. The fractions containing the product are combined and the solvent is evaporated under vacuum. The initially oily residue is crystallized by stirring with 35 ml petroleum ether.

Source