Sodium Cyanide → 5-Bromopyrimidine-2-carbonitrile

HRID 1714907Notes

Reaction equation

HRID 1714907 reaction equation
[C-:1]#[N:2].[Na+].[Br:4][C:5]1[CH:6]=[N:7][C:8](Cl)=[N:9][CH:10]=1>CN(C)C=O.O>[Br:4][C:5]1[CH:6]=[N:7][C:8]([C:1]#[N:2])=[N:9][CH:10]=1

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 6066655-Bromo-2-chloropyrimidine

Product 1

HCID 6865465-Bromopyrimidine-2-carbonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium cyanide (2.30 g, 46.6 mmol) was dissolved in dimethylformamide (60 ml) and treated with 5-bromo-2-chloropyrimidine (6.0 g, 31.1 mmol). The resulting mixture was stirred at room temperature for 18 hours, diluted with water and extracted with dichloromethane. The dichloromethane extracts were combined, washed with water, dried (magnesium sulphate), filtered and concentrated in vacuo. The crude product was purified by column chromatography eluting with a mixture of ethyl acetate:hexane (1:4) to afford the title compound (D38).

Workup

  1. extractionextracted with dichloromethane
  2. washwashed with water
  3. dry with materialdried (magnesium sulphate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by column chromatography
  7. washeluting with a mixture of ethyl acetate:hexane (1:4)

Sources & evidence

ORD record
ord-f6c65169a63d4b6285370d19171015e0
Source dataset
uspto-grants-2010_09
Patent number
US07799773B2

Reaction notes

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