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

HRID 635196

Reaction equation

HRID 635196 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[NH:20][C:19](=[O:21])[C:18]2[C:13](=[C:14](I)[CH:15]=[CH:16][CH:17]=2)[N:12]=1)[CH2:2][CH3:3].C(N(CCCC)CCCC)CCC.[CH2:36]=[CH:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C>[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[NH:20][C:19](=[O:21])[C:18]2[C:13](=[C:14]([CH:36]=[CH:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH:15]=[CH:16][CH:17]=2)[N:12]=1)[CH2:2][CH3:3]

Participants

8

Reactant 4

HCID 7622TributylamineHCID 116101-HepteneHCID 80271Tri-o-tolylphosphineHCID 1355493722-(2-n-Propoxyphenyl)-8-Iodoquinazolin-4(3H)-One

Product 1

HCID 1361324752-(2-n-Propoxyphenyl)-8-(1-Hepten-1-yl)Quinazolin-4(3H)-One

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

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.

Workup

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

Sources & evidence

ORD record
ord-ba80d6ece68343afbfd689bba07309fb
Source dataset
uspto-grants-2001_02
Patent number
US06187779B1

Linked notes

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