Ethyl cyanoacetate → Ethyl (5-bromopyrimidin-2-yl)(cyano)acetate

HRID 2421930Notes

Reaction equation

HRID 2421930 reaction equation
[H-].[Na+].[C:3]([CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])#[N:4].[Br:11][C:12]1[CH:13]=[N:14][C:15](Br)=[N:16][CH:17]=1>O1CCCC1>[Br:11][C:12]1[CH:13]=[N:14][C:15]([CH:5]([C:3]#[N:4])[C:6]([O:8][CH2:9][CH3:10])=[O:7])=[N:16][CH:17]=1

Participants

5

Reactant 3

HCID 7764Ethyl cyanoacetateHCID 24758Sodium hydrideHCID 109555882,5-Dibromopyrimidine

Product 1

HCID 13289226Ethyl (5-bromopyrimidin-2-yl)(cyano)acetateYield 24%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a chilled stirred suspension of sodium hydride (60% in oil, 34.55 mmol) in tetrahydrofuran (20 mL) was added 1.17 g of ethyl cyanoacetate (10.34 mmol) portionwise over 10 minutes. After effervescence has ceased, the yellow cloudy mixture was left to warm up to room temperature whilst stirring. 2.00 g of 5-bromo,2-bromo-pyrimidine (10.34 mmol) in 30 mL of tetrahydrofuran was added. And the mixture was left to stir at room temperature for six hours. The resultant brown mixture was concentrated under reduced pressure to give a bright brown precipitate to which water (200 mL) was added. After extraction with heptane (200 mL), the aqueous phase was acidified by the addition of HCl 1M and the resultant precipitate was collected by filtration to give on drying ethyl (5-bromopyrimidin-2-yl)(cyano)acetate as a bright brown powder (0.67 g, yield=24%).

Workup

  1. waitthe yellow cloudy mixture was left
  2. stirringwhilst stirring
  3. waitAnd the mixture was left
  4. stirringto stir at room temperature for six hours
  5. concentrationThe resultant brown mixture was concentrated under reduced pressure
  6. customto give a bright brown precipitate to which water (200 mL)
  7. additionwas added
  8. extractionAfter extraction with heptane (200 mL)
  9. additionthe aqueous phase was acidified by the addition of HCl 1M
  10. filtrationthe resultant precipitate was collected by filtration
  11. customto give

Sources & evidence

ORD record
ord-8d5e375542fd452ab7b2c35e6b4098aa
Source dataset
uspto-grants-2011_06
Patent number
US07960391B2

Reaction notes

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