Propargyl bromide → HCID 21256391, compound

HRID 1276052Notes

Reaction equation

HRID 1276052 reaction equation
[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([N:9]2[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[N:11]3[CH:20]=[CH:21][N:22]=[C:10]23)=[C:4]([F:23])[CH:3]=1.[CH2:24](Br)[C:25]#[CH:26].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:1][C:2]1[C:7]([O:8][CH2:26][C:25]#[CH:24])=[CH:6][C:5]([N:9]2[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:18])([F:19])[F:17])[N:11]3[CH:20]=[CH:21][N:22]=[C:10]23)=[C:4]([F:23])[CH:3]=1

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 22114889HCID 22114889, compound

Product 1

HCID 21256391HCID 21256391, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 8-(4-chloro-2-fluoro-5-hydroxyphenyl)-7,8-dihydro-5-trifluoromethylimidazo[1,2-a]pyrimidin-7-one (4.3 g), propargyl bromide (2.3 g), potassium carbonate (2.1 g) and acetonitrile (100 ml) was heated to reflux for 2 hours. The solvent was distilled off under reduced pressure. The residue was added with water and extracted with ethyl acetate. The extract layer was washed with water and dried on anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was recrystallized from diisopropyl ether to give the compound of interest (4.2 g) as a milk white crystal.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 hours
  3. distillationThe solvent was distilled off under reduced pressure
  4. additionThe residue was added with water
  5. extractionextracted with ethyl acetate
  6. washThe extract layer was washed with water
  7. dry with materialdried on anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customthe residue was recrystallized from diisopropyl ether
  10. customto give the compound of interest (4.2 g) as a milk white crystal

Sources & evidence

ORD record
ord-26e0a50d22fc416884af78675e307504
Source dataset
uspto-grants-2000_12
Patent number
US06165942

Reaction notes

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