Sodium Cyanide → 5-Bromopyrimidine-2-carbonitrile

HRID 2381955Notes

Reaction equation

HRID 2381955 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5](Cl)=[N:6][CH:7]=1.[C-]#N.[Na+].[N:12]12CCN(CC1)C[CH2:13]2>CS(C)=O.O>[Br:1][C:2]1[CH:3]=[N:4][C:5]([C:13]#[N:12])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 8929Sodium CyanideHCID 9237DabcoHCID 6066655-Bromo-2-chloropyrimidine

Product 1

HCID 6865465-Bromopyrimidine-2-carbonitrileYield 439.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent2×

Procedure

5-Bromo-2-chloropyrimidine (7.51 g, 38.83 mmol) is dissolved in DMSO (20 mL) is added to a mixture of NaCN (1.9 g, 38.83 mmol) and 1,4-diazabicyclo[2,2,2]octane (0.87 g, 7.77 mmol) in DMSO (10 mL) and water (20 mL). The mixture is stirred at rt overnight, and then water (100 mL) is added. The mixture is extracted with ether (3×100 mL). The combined organic layer is dried (Na2SO4), filtered and concentrated in vacuo to afford 5-bromo-pyrimidine-2-carbonitrile (6.28 g, 88%) as a solid. MS: 184 (M+H).

Workup

  1. extractionThe mixture is extracted with ether (3×100 mL)
  2. dry with materialThe combined organic layer is dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-781065348521478da5efd01375e7fe39
Source dataset
uspto-grants-2012_09
Patent number
US08258130B2

Reaction notes

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