Hydrochloric Acid → HCID 66860208, compound

HRID 1043687Notes

Reaction equation

HRID 1043687 reaction equation
[CH2:1]([C:3]1[CH:4]=[N:5][C:6]([NH:9][NH2:10])=[N:7][CH:8]=1)[CH3:2].[C:11]([CH2:14][C:15](=O)[CH3:16])(=O)[CH3:12].Cl.[OH-].[Na+]>O>[CH2:1]([C:3]1[CH:4]=[N:5][C:6]([N:9]2[C:15]([CH3:16])=[CH:14][C:11]([CH3:12])=[N:10]2)=[N:7][CH:8]=1)[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 31261AcetylacetoneHCID 45080062HCID 45080062, compound

Product 1

HCID 66860208HCID 66860208, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5-Ethyl-2-hydrazinopyrimidine (400 mg, 2.89 mmol) was suspended in 3 mL of water, and acetylacetone (314 μL, 3.04 mmol) and 2 mol/L hydrochloric acid (330 μL) were added thereto and stirred at room temperature for 23 hours. 2 mL of sodium hydroxide aqueous solution was added to the reaction mixture to adjust the pH to 12. The mixture was extracted with ethyl acetate three times, and the organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, and then filtrated. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=90:10→10:90) and silica gel column chromatography (methylene chloride:methanol=100:0→95:5) to give 203 mg of the title compound (yield 35%).

Workup

  1. extractionThe mixture was extracted with ethyl acetate three times
  2. washthe organic phase was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltrated
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=90:10→10:90) and silica gel column chromatography (methylene chloride:methanol=100:0→95:5)

Sources & evidence

ORD record
ord-4b5c5430b94047adaafe0df1caf05116
Source dataset
uspto-grants-2013_10
Patent number
US08563552B2

Reaction notes

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