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

HRID 967024Notes

Reaction equation

HRID 967024 reaction equation
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

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 783445-Bromopyrimidine

Product 1

HCID 53438539Ethyl 3-(pyrimidin-5-yl)prop-2-enoateYield 71.9%

Reagents, catalysts & solvents 3

HCID 11776TriphenylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-0cb52633a7834832ad6adbc7ef765fde
Source dataset
uspto-grants-2005_10
Patent number
US06953803B1

Reaction notes

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