Potassium Carbonate → 2-Amino-3-cyano-4-methyl-5-ethynylpyridine

HRID 1078242Notes

Reaction equation

HRID 1078242 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH3:10])[C:5]([C:11]#[C:12][Si](C)(C)C)=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+]>CO>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH3:10])[C:5]([C:11]#[CH:12])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 197071982-Amino-3-cyano-4-methyl-5-(trimethylsilylethynyl)pyridine

Product 1

HCID 233567022-Amino-3-cyano-4-methyl-5-ethynylpyridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2.8 grams (0.012 mole) of 2-amino-3-cyano-4-methyl-5-(trimethylsilylethynyl)pyridine and 1.8 grams (0.012 mole) of potassium carbonate in 100 mL of methanol is stirred at ambient temperature for one hour. The reaction mixture is then concentrated under reduced pressure to a residue. The residue is taken up in about 150 mL of water, and the solution is extracted with two 250 mL portions of diethyl ether. The combined extracts are dried with magnesium sulfate and filtered. The filtrate is concentrated under reduced pressure, yielding 2-amino-3-cyano-4-methyl-5-ethynylpyridine.

Workup

  1. concentrationThe reaction mixture is then concentrated under reduced pressure to a residue
  2. extractionthe solution is extracted with two 250 mL portions of diethyl ether
  3. dry with materialThe combined extracts are dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-47c5237d19ec4855aa10deed945195a6
Source dataset
uspto-grants-1996_08
Patent number
US05547954

Reaction notes

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