Triethylamine → (E)-Ethyl 3-(5-amino-2-iodopyrimidin-4-yl)acrylate

HRID 1799577Notes

Reaction equation

HRID 1799577 reaction equation
[I:1][C:2]1[N:7]=[C:6](I)[C:5]([NH2:9])=[CH:4][N:3]=1.C(N(CC)CC)C.[C:17]([O:21][CH2:22][CH3:23])(=[O:20])[CH:18]=[CH2:19]>O1CCOCC1.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[NH2:9][C:5]1[C:6](/[CH:19]=[CH:18]/[C:17]([O:21][CH2:22][CH3:23])=[O:20])=[N:7][C:2]([I:1])=[N:3][CH:4]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 8821Ethyl AcrylateHCID 582166432,4-Diiodopyrimidin-5-amine

Product 1

HCID 58216629(E)-Ethyl 3-(5-amino-2-iodopyrimidin-4-yl)acrylate

Reagents, catalysts & solvents 3

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A 3-necked roundbottom flask was purged and maintained under an atmosphere of nitrogen. 2,4-Diiodopyrimidin-5-amine (135 g, 389.4 mmol) in dioxane (1400 ml) was added followed by palladium(II) acetate (4.8 g, 19.63 mmol), triethylamine (157 g, 1.55 mol), ethyl acrylate (390 g, 3.90 mol), and tetrabutylammonium chloride (108 g, 389.9 mmol). The resulting solution was allowed to react, with stirring, for 16 hours while the temperature was maintained at 90° C. Upon completion, the mixture was concentrated under reduced pressure. The resulting residue was purified via silica gel chromatography eluting with 1:4 to 1:1 ethyl acetate/petroleum ether to afford the title compound.

Workup

  1. customA 3-necked roundbottom flask was purged
  2. temperaturemaintained under an atmosphere of nitrogen
  3. customto react
  4. concentrationUpon completion, the mixture was concentrated under reduced pressure
  5. customThe resulting residue was purified via silica gel chromatography
  6. washeluting with 1:4 to 1:1 ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-51a338a645dc43a3a71091f1c69ca483
Source dataset
uspto-grants-2013_01
Patent number
US08344144B2

Reaction notes

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