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Water → 3-Ethynylpyridine-2,6-diamine

HRID 77834
Notes
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Reaction equation

HRID 77834 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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-9bfab83f2eb7466e9bc8c3324ee34706
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08841327B2

Reaction notes

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