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Diethyl Ether → 3-[3-(5-Isopropyl-2,6-dimethoxy-pyrimidine-4-carbonyl)-5-methyl-phenyl]-acrylonitrile

HRID 426182
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 426182
Br[C:2]1[CH:3]=[C:4]([C:9]([C:11]2[C:16]([CH:17]([CH3:19])[CH3:18])=[C:15]([O:20][CH3:21])[N:14]=[C:13]([O:22][CH3:23])[N:12]=2)=[O:10])[CH:5]=[C:6]([CH3:8])[CH:7]=1.C([O-])(=O)C.[Na+].[C:29](#[N:32])[CH:30]=[CH2:31].CCOCC>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(=O)OCC>[CH:17]([C:16]1[C:11]([C:9]([C:4]2[CH:3]=[C:2]([CH:31]=[CH:30][C:29]#[N:32])[CH:7]=[C:6]([CH3:8])[CH:5]=2)=[O:10])=[N:12][C:13]([O:22][CH3:23])=[N:14][C:15]=1[O:20][CH3:21])([CH3:19])[CH3:18]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 3283Diethyl EtherHCID 7855AcrylonitrileHCID 517045Sodium AcetateHCID 59686860(3-Bromo-5-methyl-phenyl)-(5-isopropyl-2,6-dimethoxy-pyrimidin-4-yl)-methanone

Produkt 1

HCID 667055443-[3-(5-Isopropyl-2,6-dimethoxy-pyrimidine-4-carbonyl)-5-methyl-phenyl]-acrylonitrileAusbeute 17 %

Reagenzien, Katalysatoren, Lösungsmittel

4
HCID 167845palladium(II) acetateKatalysatorHCID 178418397HCID 178418397, VerbindungKatalysatorHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
111 °C

Versuchsvorschrift

To a stirred solution of (3-bromo-5-methyl-phenyl)-(5-isopropyl-2,6-dimethoxy-pyrimidin-4-yl)-methanone (3.79 g, 10 mmol) in anhydrous DMF (10 ml), was added sodium acetate (902 mg, 1 mmol), palladium acetate (224 mg, 1 mmol), tetrakis(triphenylphosphine)palladium(0) (1.049 g, 4 mmol), and acrylonitrile in this order. The mixture was then stirred at 90-132° C. (oil bath) for ca. 23 hr. After cooling to room temperature, ether and EA (2:1) was added to the reaction mixture. The mixture was then washed with aqueous saturated sodium bicarbonate solution, washed with water twice, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo. The residue was purified by silica gel column chromatography (eluent, EA:hexanes (1:4)) to afford 595 mg (17%) of a white solid. Z-isomer (275 mg, 8%) was also obtained as a white solid. m.p. 144-145° C.; 1H NMR (300 MHz, CDCl3) δ 1.19 (6H, d, J=6.9 Hz), 2.42 (3H, s), 2.83 (1H, m), 3.94 (3H, s), 4.08 (3H, s), 5.92 (1H, d, J=16.8 Hz), 7.39 (1H, d, J=16.8 Hz), 7.49 (1H, s), 7.69 (1H, s), 7.75 (1H, s). Z isomer: 1H NMR (300 MHz, CDCl3) δ 1.19 (6H, d, J=7.2 Hz), 2.45 (3H, s), 2.84 (1H, m), 3.93 (3H, s), 4.06 (3H, s), 5.49 (1H, d, J=12.0 Hz), 7.11 (1H, d, J=12.0 Hz), 7.75 (1H, s), 7.90 (1H, s), 7.97 (1H, s).

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. washThe mixture was then washed with aqueous saturated sodium bicarbonate solution
  3. washwashed with water twice
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was purified by silica gel column chromatography (eluent, EA:hexanes (1:4))

Quellen und Nachweise

ORD-Eintrag
ord-6518990ae20145da851be62dfed149d5
Quelldatensatz
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08106064B2

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