Sodium Cyanide → 5-Bromopyrimidine-2-carbonitrile

HRID 1046101Notes

Reaction equation

HRID 1046101 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 522.6%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent2×

Procedure

To a solution of sodium cyanide (168.35 mg, 3.36 mmol), triethylenediamine (60 mg, 0.52 mmol) in a mixture of DMSO (0.7 mL) and water (1.4 mL) was added a solution of 5-bromo-2-chloropyrimidine (500 mg, 2.59 mmol) in DMSO (1.3 mL). The solution was stirred at rt overnight, diluted with water, and extracted with EtOAc. The combined organic layer was dried over anhydrous Na2SO4 and concentrated to give 5-bromopyrimidine-2-carbonitrile (500 mg, yield 100%, crude).

Workup

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

Sources & evidence

ORD record
ord-839c9b3a87db4f4483c82f84cdd0beb5
Source dataset
uspto-grants-2013_10
Patent number
US08569292B2

Reaction notes

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