Propargyl bromide → HCID 20027319, compound

HRID 1722702Notes

Reaction equation

HRID 1722702 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][N:5]=1)(=[O:3])[CH3:2].[CH2:11](Br)[C:12]#[CH:13].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.C1(C)C=CC=CC=1>[CH2:13]([NH:10][C:7]1[CH:8]=[CH:9][C:4]([C:1](=[O:3])[CH3:2])=[N:5][CH:6]=1)[C:12]#[CH:11]

Participants

6

Reactant 3

HCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 218278161-(5-Aminopyridin-2-yl)ethan-1-one

Product 1

HCID 20027319HCID 20027319, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 1140TolueneSolvent

Procedure

2-Acetyl-5-aminopyridine, (Journal of Heterocyclic Chemistry, Vol. 10, pp. 1047-1049 (1973)), 25 g (0.161 mol), is dissolved in 600 ml of dry acetone. To this solution is added an 80% solution of propargyl bromide in toluene, 32 ml, and finely powdered potassium carbonate, 27 g. The solution is heated under reflux for thirty-six hours and then allowed to cool to room temperature. The reaction mixture is concentrated in vacuo and the residue is partitioned between dichloromethane and water. The organic portion is separated and the water layer extracted several times with dichloromethane. The combined organics are concentrated in vacuo to a semi-solid residue consisting of a mixture of starting material and a small amount of the monoalkylated product. The residue is triturated with a mixture of toluene and diethyl ether. The solid is removed by filtration and the filtrate is concentrated to an oil. Chromatography of the oil on silica gel with dichloromethane gives the desired product.

Workup

  1. temperatureThe solution is heated
  2. temperatureunder reflux for thirty-six hours
  3. concentrationThe reaction mixture is concentrated in vacuo
  4. customthe residue is partitioned between dichloromethane and water
  5. customThe organic portion is separated
  6. extractionthe water layer extracted several times with dichloromethane
  7. concentrationThe combined organics are concentrated in vacuo to a semi-solid residue
  8. additionconsisting of a mixture of starting material
  9. customThe residue is triturated with a mixture of toluene and diethyl ether
  10. customThe solid is removed by filtration
  11. concentrationthe filtrate is concentrated to an oil

Sources & evidence

ORD record
ord-0a1d31422ee645d7a699e6a26f11a5ad
Source dataset
uspto-grants-1989_08
Patent number
US04857530

Reaction notes

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