Pyridine → 5-Ethyl-4-(furan-2-yl)-pyrimidine

HRID 1527642Notes

Reaction equation

HRID 1527642 reaction equation
[CH2:1]([C:3]1[C:4](NN)=[N:5][CH:6]=[N:7][C:8]=1[C:9]1[O:10][CH:11]=[CH:12][CH:13]=1)[CH3:2].C(#N)C.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.N1C=CC=CC=1>O>[CH2:1]([C:3]1[C:8]([C:9]2[O:10][CH:11]=[CH:12][CH:13]=2)=[N:7][CH:6]=[N:5][CH:4]=1)[CH3:2]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6342AcetonitrileHCID 73974-Toluenesulfonyl chlorideHCID 67814467[5-Ethyl-6-(furan-2-yl)-pyrimidin-4-yl]-hydrazine

Product 1

HCID 678106955-Ethyl-4-(furan-2-yl)-pyrimidineYield 83.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of [5-ethyl-6-(furan-2-yl)-pyrimidin-4-yl]-hydrazine (2.85 g), acetonitrile (50 ml), and para-toluensulfonyl chloride (2.86 g), pyridine (2.37 g) was added under ice-cooling, and the reaction mixture was stirred at room temperature for 2 hours. To the reaction mixture, water (50 ml) was added, and the precipitated solids were collected by filtration. The solid was sequentially washed with water (20 ml) and acetonitrile (20 ml), and dried. To the resulting solid, sodium hydroxide (8.1 g), ethylene glycol (100 ml), and water (50 ml) were added, and stirred under reflux for 3 hours. After standing to cool the reaction mixture to room temperature, to the reaction mixture, water was added, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 2.03 g of 5-ethyl-4-furan-2-yl-pyrimidine.

Workup

  1. additionwas added under ice-
  2. temperaturecooling
  3. filtrationthe precipitated solids were collected by filtration
  4. washThe solid was sequentially washed with water (20 ml) and acetonitrile (20 ml)
  5. customdried
  6. additionTo the resulting solid, sodium hydroxide (8.1 g), ethylene glycol (100 ml), and water (50 ml) were added
  7. stirringstirred
  8. temperatureunder reflux for 3 hours
  9. temperatureto cool the reaction mixture to room temperature
  10. additionto the reaction mixture, water was added
  11. extractionextracted with ethyl acetate
  12. dry with materialThe organic layer was dried over sodium sulfate
  13. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0a8cf7e34ed64b32a65ed4ab6f1ff8e7
Source dataset
uspto-grants-2015_07
Patent number
US09089136B2

Reaction notes

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