Tetrabutylammonium Fluoride → HCID 18785839, compound

HRID 1107732Notes

Reaction equation

HRID 1107732 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[ClH:19].[NH2:20][C:21]1[C:26]2[S:27][C:28]([Si](C)(C)C)=[CH:29][C:25]=2[CH2:24][CH:23]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[N:22]=1>C1COCC1>[ClH:19].[NH2:20][C:21]1[C:26]2[S:27][CH:28]=[CH:29][C:25]=2[CH2:24][CH:23]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[N:22]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 18785870HCID 18785870, compound

Product 1

HCID 18785839HCID 18785839, compoundYield 52.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetra-n-butylammonium fluoride (1.0M in THF, 1.12 ml), was added dropwise to a solution of 7-amino-5-phenyl-2-trimethylsilyl-4,5-dihydrothieno[2,3-c]pyridine hydrochloride (0.13 g, 0.37 mmol) in THF (2.5 ml) and the mixture stirred for 30 min., evaporated and the residue purified by flash chromatography on untreated neutral alumina, eluting with 4% methanol in dichloromethane, increasing the gradient by increments to 20% methanol in dichloromethane to afford a colourless glass. Recrystallisation from dichloromethane gave the title compound as white crystals (51 mg), m.p. 234-236° C.

Workup

  1. customevaporated
  2. customthe residue purified by flash chromatography on untreated neutral alumina
  3. washeluting with 4% methanol in dichloromethane
  4. temperatureincreasing the gradient by increments to 20% methanol in dichloromethane
  5. customto afford a colourless glass
  6. customRecrystallisation from dichloromethane

Sources & evidence

ORD record
ord-698ed6514c9c470788f1854f11a974ec
Source dataset
uspto-grants-2000_05
Patent number
US06063789

Reaction notes

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