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

HRID 1241604Notes

Reaction equation

HRID 1241604 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 pet ether to obtain ethyl 3-(5-pyrimidyl)acrylate (4.78 g). 1H-NMR (CDCl3) δ 1.36 (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 pet ether

Sources & evidence

ORD record
ord-46cc1ef97f114b2ea96512ee5232f45d
Source dataset
uspto-grants-2006_10
Patent number
US07115616B2

Reaction notes

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