Propargyl bromide → HCID 22114887, compound

HRID 1276053Notes

Reaction equation

HRID 1276053 reaction equation
[C:1]([C:3]1[C:8]([OH:9])=[CH:7][C:6]([N:10]2[C:15](=[O:16])[CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[N:12]3[CH:21]=[CH:22][N:23]=[C:11]23)=[C:5]([F:24])[CH:4]=1)#[N:2].[CH2:25](Br)[C:26]#[CH:27].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:1]([C:3]1[C:8]([O:9][CH2:27][C:26]#[CH:25])=[CH:7][C:6]([N:10]2[C:15](=[O:16])[CH:14]=[C:13]([C:17]([F:18])([F:20])[F:19])[N:12]3[CH:21]=[CH:22][N:23]=[C:11]23)=[C:5]([F:24])[CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 22114884HCID 22114884, compound

Product 1

HCID 22114887HCID 22114887, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 8-(4-cyano-2-fluoro-5-hydroxyphenyl)-7,8-dihydro-5-trifluoromethylimidazo[1,2-a]pyrimidin-7-one (0.23 g), propargyl bromide (0.16 g), potassium carbonate (0.14 g) and acetonitrile (15 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 (0.17 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 (0.17 g) as a milk white crystal

Sources & evidence

ORD record
ord-72c9318438754feb81948b4104ab5438
Source dataset
uspto-grants-2000_12
Patent number
US06165942

Reaction notes

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