Water → HCID 117759541, compound

HRID 709815Notes

Reaction equation

HRID 709815 reaction equation
[Br:1][C:2]1[C:3]([O:9][CH2:10][CH:11]([CH3:13])[CH3:12])=[N:4][C:5](Cl)=[N:6][CH:7]=1.[N:14]12CCN(CC1)C[CH2:15]2.O>C(#N)C.[C-]#N.C([N+](CC)(CC)CC)C>[Br:1][C:2]1[C:3]([O:9][CH2:10][CH:11]([CH3:13])[CH3:12])=[N:4][C:5]([C:15]#[N:14])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 962WaterHCID 9237DabcoHCID 79075816HCID 79075816, compound

Product 1

HCID 117759541HCID 117759541, compoundYield 82.1%

Reagents, catalysts & solvents 2

HCID 3014735Tetraethylammonium cyanideCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of 5-bromo-2-chloro-4-isobutoxypyrimidine (2.16 g) and 1,4-diazabicyclo[2.2.2]octane (1.83 g) in acetonitrile (30 mL) was added tetraethylammonium cyanide (1.40 g), and the mixture was stirred at room temperature for 30 min. To the reaction mixture was added water at room temperature, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (1.71 g) as a colorless oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-1d147391ac1746caa308e498d299713f
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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