Water → 6-Methoxypyrimidine-4-carbonitrile

HRID 709606Notes

Reaction equation

HRID 709606 reaction equation
Cl[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[N:5]=[CH:4][N:3]=1.[N:10]12CCN(CC1)C[CH2:11]2.O>C(#N)C.[C-]#N.C([N+](CC)(CC)CC)C>[CH3:9][O:8][C:6]1[N:5]=[CH:4][N:3]=[C:2]([C:11]#[N:10])[CH:7]=1

Participants

6

Reactant 3

HCID 962WaterHCID 9237DabcoHCID 10515094-Chloro-6-methoxypyrimidine

Product 1

HCID 592380226-Methoxypyrimidine-4-carbonitrileYield 60.9%

Reagents, catalysts & solvents 2

HCID 3014735Tetraethylammonium cyanideCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-chloro-6-methoxypyrimidine (10.6 g) in acetonitrile (150 mL) was added 1,4-diazabicyclo[2.2.2]octane (8.18 g), and the mixture was stirred at room temperature for 10 min. Tetraethylammonium cyanide (11.5 g) was added to the obtained reaction mixture, and the mixture was stirred at room temperature for 3 hr. Water was added to the reaction mixture 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 (6.00 g) as a pale-yellow oil.

Workup

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

Sources & evidence

ORD record
ord-73dcc7eaf0064ba6b7abfa6867e3c55d
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

Loading…