Sodium Hydroxide → 5-Bromo-4-chloro-6-ethylpyrimidine

HRID 129473Notes

Reaction equation

HRID 129473 reaction equation
O[C:2]1[C:7]([Br:8])=[C:6]([CH2:9][CH3:10])[N:5]=[CH:4][N:3]=1.P(Cl)(Cl)([Cl:13])=O.[OH-].[Na+]>>[Cl:13][C:2]1[C:7]([Br:8])=[C:6]([CH2:9][CH3:10])[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 178437740HCID 178437740, compound

Product 1

HCID 212526725-Bromo-4-chloro-6-ethylpyrimidine

Conditions

Temperature
70 °C

Procedure

29.7 g (0.146 mol) of 4-hydroxy-5-bromo-6-ethylpyrimidine are introduced slowly into 27.3 g (0.178 mol) of phosphorus oxychloride. The suspension dissolves on heating to 70° C.; the reaction is slightly exothermic. The temperature is kept at 70° C. for 11/2 hours and, after cooling, the solution is poured onto ice-water and neutralised carefully to pH 5-7, at 0° C., with 30% sodium hydroxide solution. Extraction with ethyl acetate yields, after removal of the solvent, 30.4 g of crude product. Distillation yields 23.9 g (73.9% of the theoretical yield) of pure substance having a boiling point of 112°-114° C./24 mbar.

Workup

  1. dissolutionThe suspension dissolves
  2. customis kept at 70° C. for 11
  3. custom2 hours
  4. temperatureafter cooling
  5. extractionExtraction with ethyl acetate
  6. customyields
  7. customafter removal of the solvent, 30.4 g of crude product
  8. distillationDistillation
  9. customyields 23.9 g (73.9% of the
  10. customtheoretical yield) of pure substance

Sources & evidence

ORD record
ord-94fbb62028274606be891f1e7f2652c1
Source dataset
uspto-grants-1995_11
Patent number
US05468751

Reaction notes

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