Water → 3-Ethynylpyridine-2,6-diamine

HRID 1693787Notes

Reaction equation

HRID 1693787 reaction equation
C[Si]([C:5]#[C:6][C:7]1[C:8]([NH2:14])=[N:9][C:10]([NH2:13])=[CH:11][CH:12]=1)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1>[C:6]([C:7]1[C:8]([NH2:14])=[N:9][C:10]([NH2:13])=[CH:11][CH:12]=1)#[CH:5]

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 592554712,6-Pyridinediamine, 3-[2-(trimethylsilyl)ethynyl]-

Product 1

HCID 552816763-Ethynylpyridine-2,6-diamineYield 73.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-trimethylsilanylethynyl-pyridin-2,6-diamine (7.0 g, 34.1 mmol.) described in Manufacturing Example 13-1-2 in tetrahydrofuran (100 mL) was added tetrabutylammonium fluoride (1M tetrahydrofuran solution, 17 mL, 17 mmol) on an ice bath, which was stirred for 10 minutes at room temperature. Water was added to the reaction solution, which was then extracted with ethyl acetate 3 times. The extract was dried over sodium sulfate, and the solvent was evaporated under a reduced pressure. The residue was purified by silica gel chromatography (ethyl acetate) to obtain the title compound (3.35 g, 73.8%).

Workup

  1. extractionwas then extracted with ethyl acetate 3 times
  2. dry with materialThe extract was dried over sodium sulfate
  3. customthe solvent was evaporated under a reduced pressure
  4. customThe residue was purified by silica gel chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-b054f384f6ed4924a2a6958faa5ff0f1
Source dataset
uspto-grants-2012_04
Patent number
US08158657B2

Reaction notes

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