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Tetrabutylammonium Fluoride → 1-(2-Chloro-7-(pentan-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl)ethanol

HRID 2189326
Notes
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Reaction equation

HRID 2189326 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH:9]([CH2:12][CH3:13])[CH2:10][CH3:11])[C:5]([C:14]#[C:15][CH:16]([OH:18])[CH3:17])=[CH:4][N:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.O>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[CH:14]=[C:15]([CH:16]([OH:18])[CH3:17])[N:8]([CH:9]([CH2:12][CH3:13])[CH2:10][CH3:11])[C:6]=2[N:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 866373494-[2-Chloro-4-(1-ethyl-propylamino)-pyrimidin-5-yl]-but-3-yn-2-ol

Product 1

HCID 735546611-(2-Chloro-7-(pentan-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl)ethanolYield 52.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[2-chloro-4-(1-ethyl-propylamino)-pyrimidin-5-yl]-but-3-yn-2-ol (0.23 g, 0.85 mmol) in THF (0.5 mL) is added 1M TBAF (4.3 mL). The reaction mixture is heated at reflux for 16 h, diluted with water, extracted with EtOAc. The extracts are dried over Na2SO4 and concentrated in vacuo. The residue is purified by flash chromatography (SiO2, EtOAc/Hexane 1:3) to provide 0.12 g of 1-[2-chloro-7-(1-ethyl-propyl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-ethanol.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 16 h
  3. extractionextracted with EtOAc
  4. dry with materialThe extracts are dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by flash chromatography (SiO2, EtOAc/Hexane 1:3)

Sources & evidence

ORD record
ord-36f0704d68b54640ad4b8f0c8447139d
Source dataset
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08324225B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes