Water → 3-Ethynylpyridine-2,6-diamine

HRID 640116Notes

Reaction equation

HRID 640116 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-b6862cfce49d44a2b9ccc9b094563608
Source dataset
uspto-grants-2010_04
Patent number
US07691882B2

Reaction notes

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