Dimethyl Sulfoxide → 5-Bromopyrimidine-2-carbonitrile

HRID 1374153Notes

Reaction equation

HRID 1374153 reaction equation
CS(C)=O.[Br:5][C:6]1[CH:7]=[N:8][C:9](Cl)=[N:10][CH:11]=1.[C-:13]#[N:14].[Na+]>O.CCOC(C)=O>[Br:5][C:6]1[CH:7]=[N:8][C:9]([C:13]#[N:14])=[N:10][CH:11]=1

Participants

6

Reactant 3

HCID 679Dimethyl SulfoxideHCID 8929Sodium CyanideHCID 6066655-Bromo-2-chloropyrimidine

Product 1

HCID 6865465-Bromopyrimidine-2-carbonitrileYield 82.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a room temperature DMSO solution (20.0 mL) of 5-bromo-2-chloropyrimidine (1.02 g, 5.27 mmol) was added sodium cyanide (0.284 g, 5.80 mmol). After 70 minutes the reaction mixture was diluted with water (300 mL) and EtOAc (150 mL). The organic layer was washed three times with half brine, then once with brine. The organic layer was dried over sodium sulfate, filtered and evaporated under reduced pressure to obtain a residue, which was subject to silica gel chromatography. Collection of the product containing fractions and removal of solvent provided 5-bromopyrimidine-2-carbonitrile (0.800 g) as a white crystalline solid, giving proton NMR and LC/MS data consistent with theory.

Workup

  1. washThe organic layer was washed three times with half brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated under reduced pressure
  5. customto obtain a residue, which
  6. customCollection of the product
  7. additioncontaining
  8. customfractions and removal of solvent

Sources & evidence

ORD record
ord-eb22bdefe00f4dd09c25aeb9eb9f025c
Source dataset
uspto-grants-2007_01
Patent number
US07163951B2

Reaction notes

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