Sodium Iodide → 5-(5-Iodopyridin-2-yloxy)pyrimidine

HRID 76132Notes

Reaction equation

HRID 76132 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:10]=[N:11][CH:12]=[N:13][CH:14]=2)=[N:6][CH:7]=1.O1CCOCC1.[Na+].[I-:22].CN(C)CCN>CCOC(C)=O.[Cu]I>[I:22][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:10]=[N:11][CH:12]=[N:13][CH:14]=2)=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 312751,4-DioxaneHCID 66053N,N-DimethylethylenediamineHCID 666115945-(5-Bromopyridin-2-yloxy)pyrimidine

Product 1

HCID 666347625-(5-Iodopyridin-2-yloxy)pyrimidine

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 550 mg (2.18 mmol) 5-(5-bromopyridin-2-yloxy)pyrimidine and 2.5 mL 1,4-dioxane is charged with 42 mg (0.22 mmol) CuI, 650 mg (4.36 mmol) NaI and 50 μl (0.44 mmo) N,N-dimethylethylendiamine. The reaction mixture is stirred at 110° C. over night. The mixture is allowed to cool down to r.t. and diluted with EtOAc. The mixture is washed with 5% aq. ammonia solution and water. The organic layer is dried with Na2SO4 and the solvent is removed in vacuo to yield the desired product without further purification.

Workup

  1. temperatureto cool down to r.t.
  2. washThe mixture is washed with 5% aq. ammonia solution and water
  3. dry with materialThe organic layer is dried with Na2SO4
  4. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-4aa93c5a560c44e086cbff263d57e443
Source dataset
uspto-grants-2014_09
Patent number
US08835472B2

Reaction notes

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