Potassium Carbonate → 3-Chloro-5-ethynyl-2-methylthiopyridine

HRID 368291Notes

Reaction equation

HRID 368291 reaction equation
[Cl:1][C:2]1[C:3]([S:14][CH3:15])=[N:4][CH:5]=[C:6]([C:8]#[C:9][Si](C)(C)C)[CH:7]=1.C(=O)([O-])[O-].[K+].[K+]>CO>[Cl:1][C:2]1[C:3]([S:14][CH3:15])=[N:4][CH:5]=[C:6]([C:8]#[CH:9])[CH:7]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 232882763-Chloro-2-methylthio-5-(trimethylsilylethynyl)-pyridine

Product 1

HCID 232882663-Chloro-5-ethynyl-2-methylthiopyridineYield 98.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-Chloro-2-methylthio-5-(trimethylsilylethynyl)-pyridine (1.1 g, 4.3 mmol) was dissolved with stirring in methanol (50 mL) and anhydrous potassium carbonate (2.5 g, 0.018 mol) added. The mixture was stirred overnight, filtered, and evaporated to dryness. The residue was slurried in dichloromethane (100 mL), filtered, and evaporated to dryness. The residue was purified by chromatography over silica (0-3% ethyl acetate:hexane) to give the desired product (0.78 g, 95%) as a pale solid which darkens on standing, melting point. 58-60° C.

Workup

  1. filtrationfiltered
  2. customevaporated to dryness
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe residue was purified by chromatography over silica (0-3% ethyl acetate:hexane)

Sources & evidence

ORD record
ord-635c32cc49be4cb88dbe31e7b7aad6df
Source dataset
uspto-grants-2000_10
Patent number
US06133294

Reaction notes

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