Triethylamine → Ethyl 3-(pyrimidin-5-yl)prop-2-enoate

HRID 967024Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 967024
Br[C:2]1[CH:3]=[N:4][CH:5]=[N:6][CH:7]=1.[C:8]([O:12][CH2:13][CH3:14])(=[O:11])[CH:9]=[CH2:10].C(N(CC)CC)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[N:4]1[CH:3]=[C:2]([CH:10]=[CH:9][C:8]([O:12][CH2:13][CH3:14])=[O:11])[CH:7]=[N:6][CH:5]=1

Komponenten

7

Edukt 3

HCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 783445-Bromopyrimidine

Produkt 1

HCID 53438539Ethyl 3-(pyrimidin-5-yl)prop-2-enoateAusbeute 71,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11776TriphenylphosphineKatalysatorHCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A mixture of 5-bromopyrimidine (5.93 g), ethyl acrylate (5.08 g), palladium acetate (0.112 g), triphenyl phosphine (0.23 g) and triethylamine (4.5 g) was stirred at 150° C. in a-pressure vessel for 6 hours. After cooling overnight, water (50 ml) was added to the dark residue, and the product was extracted into toluene. Drying, charcoaling and evaporation gave a pale oil, which was triturated with peL ether to obtain ethyl 3(5-pyrimidyl)acrylate (4.78 g). 1H-NMR (CDCl3) δ1.36 (3H,t), 4.27 (2H,q), 6.59 (1H,d), 7.62 (1H,d), 8.88 (2H,s), 9.20 (1H,s).

Aufarbeitung

  1. temperatureAfter cooling overnight
  2. extractionthe product was extracted into toluene
  3. customDrying
  4. customcharcoaling and evaporation
  5. customgave a pale oil, which
  6. customwas triturated with peL ether

Quellen und Nachweise

ORD-Eintrag
ord-0cb52633a7834832ad6adbc7ef765fde
Quelldatensatz
uspto-grants-2005_10
Patentnummer
US06953803B1

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