Potassium Carbonate → 5-Ethynylpyridin-3-amine

HRID 1098589Notes

Reaction equation

HRID 1098589 reaction equation
C[Si](C)(C)[C:3]#[C:4][C:5]1[CH:6]=[C:7]([NH2:11])[CH:8]=[N:9][CH:10]=1.C([O-])([O-])=O.[K+].[K+]>CO>[C:4]([C:5]1[CH:6]=[C:7]([NH2:11])[CH:8]=[N:9][CH:10]=1)#[CH:3]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 58235284HCID 58235284, compound

Product 1

HCID 210712745-Ethynylpyridin-3-amineYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-(2-(trimethylsilyl)ethynyl)pyridin-3-amine (0.279 g, 1.466 mmol) in MeOH (2.0 mL) was added K2CO3 (0.304 g, 2.20 mmol). The reaction was stirred at RT overnight. Solvent was removed under reduced pressure and the residue was extracted with EtOAc (2×). The combined organic layers were washed with H2O (1×) and brine (1×), dried (MgSO4) and concentrated to afford 5-ethynylpyridin-3-amine (0.168 g, 97%) as a light yellow solid.

Workup

  1. customSolvent was removed under reduced pressure
  2. extractionthe residue was extracted with EtOAc (2×)
  3. washThe combined organic layers were washed with H2O (1×) and brine (1×)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-01f890d997f142f48ca7887f0f914cad
Source dataset
uspto-grants-2012_03
Patent number
US08143293B2

Reaction notes

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