Tetrabutylammonium Fluoride → HCID 86706461, compound

HRID 919590Notes

Reaction equation

HRID 919590 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C@H:10]([O:14][C:15]2[C:16]3[CH:23]=[CH:22][N:21](COCC[Si](C)(C)C)[C:17]=3[N:18]=[CH:19][N:20]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[N:18]1[C:17]2[NH:21][CH:22]=[CH:23][C:16]=2[C:15]([O:14][C@H:10]2[CH2:11][CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9]2)=[N:20][CH:19]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86706458HCID 86706458, compound

Product 1

HCID 86706461HCID 86706461, compoundYield 92.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-tert-butyl-3-(7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yloxy)piperidine-1-carboxylate (0.1 g, 0.22 mmol) in THF (5 mL) was added TBAF (291 mg, 1.1 mmol) and the reaction mixture was refluxed for 5 h. The reaction mixture was cooled and was concentrated in vacuo to give a residue which was partitioned between EtOAc (25 mL) and water (25 mL). The EtOAc layer was separated and the water layer was extracted with EtOAc (3×25 mL). The combined organic layer was dried over Na2SO4 and evaporated in vacuo to give the crude compound which was purified by column chromatography (silica gel, gradient EtOAc in hexanes) to give (65 mg, 74%) the titled compound.

Workup

  1. temperaturethe reaction mixture was refluxed for 5 h
  2. temperatureThe reaction mixture was cooled
  3. concentrationwas concentrated in vacuo
  4. customto give a residue which
  5. customwas partitioned between EtOAc (25 mL) and water (25 mL)
  6. customThe EtOAc layer was separated
  7. extractionthe water layer was extracted with EtOAc (3×25 mL)
  8. dry with materialThe combined organic layer was dried over Na2SO4
  9. customevaporated in vacuo
  10. customto give the crude compound which
  11. customwas purified by column chromatography (silica gel, gradient EtOAc in hexanes)

Sources & evidence

ORD record
ord-86c82652ad9643279f76908387a4f431
Source dataset
uspto-grants-2016_03
Patent number
US09273028B2

Reaction notes

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