Triethylamine → HCID 18671034, compound

HRID 1057256Notes

Reaction equation

HRID 1057256 reaction equation
[CH2:1]([O:3][CH2:4][N:5]1[CH:12]=[C:11](I)[C:9](=[O:10])[NH:8][C:6]1=[O:7])[CH3:2].[C:14]([O:18][CH2:19][CH3:20])(=[O:17])[CH:15]=[CH2:16].C(N(CC)CC)C>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:14](/[CH:15]=[CH:16]/[C:11]1[C:9](=[O:10])[NH:8][C:6](=[O:7])[N:5]([CH2:4][O:3][CH2:1][CH3:2])[CH:12]=1)([O:18][CH2:19][CH3:20])=[O:17]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 18671028HCID 18671028, compound

Product 1

HCID 18671034HCID 18671034, compoundYield 74.4%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Then, 1.184 g (4 mmol) of 1-(ethoxymethyl)-5-iodouracil, 870 μg (8 mmol) of ethyl acrylate, 45 mg of palladium acetate and 0.6 ml of triethylamine were dissolved in 40 ml of dimethylformamide, heated and stirred for 5 hours at 70° C. After the solvent was evaporated under reduced pressure, the residue was adsorbed on a silica gel column, eluted with a solution of dichloromethan/ethyl acetate (1:1 v/v) to recover the desired fraction, from which the solvent was evaporated under reduced pressure to obtain 798 mg of 5-(2-(E)-carboethoxyvinyl)-1-(ethoxymethyl)uracil as crystals.

Workup

  1. temperatureheated
  2. customAfter the solvent was evaporated under reduced pressure
  3. washeluted with a solution of dichloromethan/ethyl acetate (1:1 v/v)
  4. customto recover the desired fraction
  5. customfrom which the solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-130d561879c8419094a81368261011e1
Source dataset
uspto-grants-2003_02
Patent number
USRE037979E1

Reaction notes

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