Potassium Carbonate → (S)-6-amino-5-ethynyl-N-[methyl(oxo)phenyl-lambda6-sulfanylidene]nicotinamide

HRID 1099653Notes

Reaction equation

HRID 1099653 reaction equation
[NH2:1][C:2]1[C:19]([C:20]#[C:21][Si](C)(C)C)=[CH:18][C:5]([C:6]([N:8]=[S@@:9]([CH3:17])(=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])=[CH:4][N:3]=1.C([O-])([O-])=O.[K+].[K+]>C1COCC1.CO>[NH2:1][C:2]1[C:19]([C:20]#[CH:21])=[CH:18][C:5]([C:6]([N:8]=[S@@:9]([CH3:17])(=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:7])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 24954185(S)-6-amino-N-[methyl(oxo)phenyl-lambda6-sulfanylidene]-5-[(trimethylsilyl)ethynyl]nicotinamide

Product 1

HCID 24954186(S)-6-amino-5-ethynyl-N-[methyl(oxo)phenyl-lambda6-sulfanylidene]nicotinamideYield 78%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of (S)-6-amino-N-[methyl(oxo)phenyl-λ6-sulfanylidene]-5-[(trimethylsilyl)ethynyl]nicotinamide (308 mg, 0.83 mmol) in 20 mL THF/methanol (1:1 ratio) at 0° C. was added K2CO3 (344 mg, 2.5 mmol) added. After 7 minutes the solution was decanted from the solids and partitioned between EtOAc and H2O. The EtOAc layer was washed with brine, dried with anhydrous Na2SO4 and rotary evaporated. The brown oil was purified by chromatography (silica gel, CHCl3/EtOAc) to give the title compound as a white solid (193 mg, 78%).

Workup

  1. additionadded
  2. customAfter 7 minutes the solution was decanted from the solids
  3. custompartitioned between EtOAc and H2O
  4. washThe EtOAc layer was washed with brine
  5. dry with materialdried with anhydrous Na2SO4 and rotary evaporated
  6. customThe brown oil was purified by chromatography (silica gel, CHCl3/EtOAc)

Sources & evidence

ORD record
ord-a806ca0693524047bdb8db45901c0193
Source dataset
uspto-grants-2012_03
Patent number
US08143410B2

Reaction notes

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