Sodium Cyanide → 5-Bromopyrimidine-2-carbonitrile

HRID 1482494Notes

Reaction equation

HRID 1482494 reaction equation
[C-]#N.[Na+].C1N2CC[N:6](CC2)[CH2:5]1.[Br:12][C:13]1[CH:14]=[N:15][C:16](Cl)=[N:17][CH:18]=1>CS(C)=O.O>[Br:12][C:13]1[CH:14]=[N:15][C:16]([C:5]#[N:6])=[N:17][CH:18]=1

Participants

6

Reactant 3

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

Product 1

HCID 6865465-Bromopyrimidine-2-carbonitrileYield 345.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent2×

Procedure

To a solution of NaCN (0.849 g, 17.32 mmol) and DABCO (0.390 g, 3.48 mmol) in a mixture of DMSO (4 ml) and H2O (9 ml) was added a solution of 5-bromo-2-chloropyrimidine (3.05 g, 15.75 mmol) in DMSO (9 ml). The solution was stirred at room temperature overnight, and then diluted with water, and extracted with EtOAc. The combined organic layer was dried over anhydrous Na2SO4 and concentrated to give 5-bromopyrimidine-2-carbonitrile (2,327 g, 12.01 mmol, 76% yield, 1H NMR (CDCl3 500 MHz): δ 8.94 (s, 2H)).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-4bac712ce9be457384aa0c737e2b9184
Source dataset
uspto-grants-2016_08
Patent number
US09415055B2

Reaction notes

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