Water → 3-Ethynylpyridin-2-amine

HRID 557257Notes

Reaction equation

HRID 557257 reaction equation
C[Si](C)(C)[C:3]1[C:4]([NH:9]C#C)=[N:5][CH:6]=[CH:7][CH:8]=1.[F-].[CH2:15]([N+](CCCC)(CCCC)CCCC)[CH2:16]CC.O>O1CCCC1>[C:15]([C:3]1[C:4]([NH2:9])=[N:5][CH:6]=[CH:7][CH:8]=1)#[CH:16]

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 131729277HCID 131729277, compound

Product 1

HCID 124225263-Ethynylpyridin-2-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-trimethylsilanyl ethinyl-pyridin-2-ylamine described in Preparation Example 1-1-4 (28.1 g, 148 mmoL) in tetrahydrofuran (300 mL) was added tetrabutyl ammonium fluoride (1M tetrahydrofuran solution, 20 mL, 20 mmol), which was stirred at room temperature for 15 minutes. To the reaction solution was added water and extracted four times with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the solvent thereof was evaporated under a reduced pressure. The residue was purified by silica gel chromatography (heptane:ethyl acetate=1:1 then 1:2) to obtain the title compound (16.4 g).

Workup

  1. extractionextracted four times with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent thereof was evaporated under a reduced pressure
  4. customThe residue was purified by silica gel chromatography (heptane

Sources & evidence

ORD record
ord-9f903909047b4e908bd720b97a88b5b1
Source dataset
uspto-grants-2011_11
Patent number
US08058444B2

Reaction notes

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