Tetrabutylammonium Fluoride → HCID 54452637, compound

HRID 361416Notes

Reaction equation

HRID 361416 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH3:19][O:20][C:21]1[C:22]([N:28](COCC[Si](C)(C)C)[S:29]([C:32]2[C:33]([C:38]3[CH:43]=[CH:42][C:41]([S:44][CH3:45])=[CH:40][CH:39]=3)=[N:34][CH:35]=[CH:36][CH:37]=2)(=[O:31])=[O:30])=[N:23][CH:24]=[C:25]([CH3:27])[N:26]=1>C1COCC1>[CH3:19][O:20][C:21]1[C:22]([NH:28][S:29]([C:32]2[C:33]([C:38]3[CH:43]=[CH:42][C:41]([S:44][CH3:45])=[CH:40][CH:39]=3)=[N:34][CH:35]=[CH:36][CH:37]=2)(=[O:31])=[O:30])=[N:23][CH:24]=[C:25]([CH3:27])[N:26]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium Fluoride3×HCID 23226635HCID 23226635, compound

Product 1

HCID 54452637HCID 54452637, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

Tetrabutylammonium fluoride (0.7 ml of a 1.1M solution in THF) was added to a solution of N-(3-methoxy-5-methylpyrazin-2-yl)-2-(4-methylthiophenyl)-N-[2-(trimethylsilyl)ethoxymethyl]pyridine-3-sulphonamide (0.373 g) in dry THF (4 ml) and the solution was heated to 60° C. for 3 hours. More tetrabutylammonium fluoride solution (0.35 ml) was added and heating was continued for 5 hours. Further aliquots of tetrabutylammonium fluoride solution (a further 2.5 ml in total) were added until reaction was complete as judged by thin layer chromatography (eluting with ethyl acetate/hexane (1:1 v/v)). Volatile material was removed by evaporation and the residue was diluted with water and extracted three times with ethyl acetate. The organic extracts were washed with water and saturated sodium chloride solution and then dried (MgSO4). Volatile material was removed by evaporation and the residue was purified by gradient elution with 0-40% ethyl acetate/hexane through a silica gel Mega Bond Elut column to give N-(3-methoxy-5-methylpyrazin-2-yl)-2-(4-methylthiophenyl)pyridine-3-sulphonamide (0.201 g) as a foam; 1H NMR (CDCl3): 2.3 (s, 3 H), 2.5 (s, 3 H), 3.8 (s, 3 H), 7.15-7.35 (m, 4 H), 7.5 (m, 1 H), 8.7 (dd, 1 H), 8.8 (dd, 1 H); mass spectrum (+ve ESP): 403 (M+H)+.

Workup

  1. temperatureheating
  2. washas judged by thin layer chromatography (eluting with ethyl acetate/hexane (1:1 v/v))
  3. customVolatile material was removed by evaporation
  4. additionthe residue was diluted with water
  5. extractionextracted three times with ethyl acetate
  6. washThe organic extracts were washed with water and saturated sodium chloride solution
  7. dry with materialdried (MgSO4)
  8. customVolatile material was removed by evaporation
  9. customthe residue was purified by gradient elution with 0-40% ethyl acetate/hexane through a silica gel Mega Bond Elut column

Sources & evidence

ORD record
ord-4d0c2a4d12514011967fefa8da8bbba5
Source dataset
uspto-grants-1999_02
Patent number
US05866568

Reaction notes

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