Hydrochloric Acid → HCID 135804111, compound

HRID 2415030Notes

Reaction equation

HRID 2415030 reaction equation
[C:1]([C:3]1[C:4]([O:14]C)=[N:5][C:6]([CH3:13])=[N:7][C:8]=1[C:9]([F:12])([F:11])[F:10])#[CH:2].[ClH:16]>>[Cl:16][C:1]([C:3]1[C:4](=[O:14])[NH:5][C:6]([CH3:13])=[N:7][C:8]=1[C:9]([F:12])([F:11])[F:10])=[CH2:2]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 121512065-Ethynyl-4-methoxy-2-methyl-6-(trifluoromethyl)pyrimidine

Product 1

HCID 135804111HCID 135804111, compound

Procedure

5-ethynyl-4-methoxy-2-methyl-6-trifluoromethylpyrimidine (1.92 g) was added 6N-HCl (20 ml) with stirring and refluxed for 2 hr. After cooling to room temperature, the reaction mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with brine and dried over magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by silica gel column chromatography (hexanethyl acetate). The crude fraction was concentrated, and then washed with hexane to give 5-(1-chlorovinyl)-2-methyl-6-trifluoromethyl-3H-pyrimidin-4-one (1.62 g) as colorless crystalline solid, mp 164-166° C.

Workup

  1. temperaturerefluxed for 2 hr
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexanethyl acetate)
  7. concentrationThe crude fraction was concentrated
  8. washwashed with hexane

Sources & evidence

ORD record
ord-2e4212e1c7174750a0a013009310fbc2
Source dataset
uspto-grants-2004_11
Patent number
US06818631B1

Reaction notes

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