5-Bromo-2-chloropyrimidine → 5-Bromo-2-ethoxypyrimidine

HRID 515919Notes

Reaction equation

HRID 515919 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5](Cl)=[N:6][CH:7]=1.[CH3:9][CH2:10][O-:11].[Na+]>C(O)C>[Br:1][C:2]1[CH:3]=[N:4][C:5]([O:11][CH2:10][CH3:9])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 6066655-Bromo-2-chloropyrimidineHCID 2723922Sodium ethoxide

Product 1

HCID 164271415-Bromo-2-ethoxypyrimidine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Bromo-2-chloro-pyrimidine (5.0 g, 25 mmol) is dissolved in ethanol (55 mL) and sodium ethylate (1.81 g, 26.6 mmol) is added in portions. The reaction mixture is stirred for 15 hours at ambient temperature. When the reaction is complete, the solvent is evaporated off, water (200 mL) is added, and then the reaction mixture is extracted with dichloromethane (2×100 mL). The organic phase is dried over Na2SO4, and then evaporated to dryness to yield 5-bromo-2-ethoxy-pyrimidine.

Workup

  1. customthe solvent is evaporated off
  2. additionwater (200 mL) is added
  3. extractionthe reaction mixture is extracted with dichloromethane (2×100 mL)
  4. dry with materialThe organic phase is dried over Na2SO4
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-01e528e0fc20442795e04c9eb57eaa67
Source dataset
uspto-grants-2015_08
Patent number
US09108983B2

Reaction notes

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