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

HRID 635196

Reaktionsgleichung

Reaktionsgleichung von HRID 635196
[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]

Komponenten

8

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-ba80d6ece68343afbfd689bba07309fb
Quelldatensatz
uspto-grants-2001_02
Patentnummer
US06187779B1

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