Hydrochloric Acid → 1-(6-Chloropyrimidin-4-yl)ethan-1-one

HRID 2401189Notes

Reaction equation

HRID 2401189 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([O:10]CC)=[CH2:9])[N:5]=[CH:4][N:3]=1.Cl>CC(C)=O>[Cl:1][C:2]1[N:3]=[CH:4][N:5]=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 865947284-Chloro-6-(1-ethoxyvinyl)pyrimidine2×

Product 1

HCID 722142471-(6-Chloropyrimidin-4-yl)ethan-1-oneYield 76.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-Chloro-6-[1-(ethyloxy)ethenyl]pyrimidine (Intermediate 17, 3.54 g, 19.17 mmol) was dissolved in acetone (177 mL), treated with 2M aqueous hydrochloric acid solution (28.8 mL, 57.5 mmol) and the resulting mixture was stirred at room temperature for 18 hours. The solvent was removed under reduced pressure. The residue was neutralised with aqueous saturated sodium bicarbonate solution and extracted with ethyl acetate (×2). The ethyl acetate layers were combined, dried under magnesium sulfate and evaporated under reduced pressure to give the title compound as a white solid (2.30 g);

Workup

  1. customThe solvent was removed under reduced pressure
  2. extractionextracted with ethyl acetate (×2)
  3. customdried under magnesium sulfate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-a7553d8829d3406b8e834eeafe3f7f94
Source dataset
uspto-grants-2014_08
Patent number
US08796283B2

Reaction notes

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