Tetrahydrofuran → 3-Ethynylpyridine-2,6-diamine

HRID 1927219Notes

Reaction equation

HRID 1927219 reaction equation
C1COCC1.C[Si]([C:10]#[C:11][C:12]1[C:13]([NH2:19])=[N:14][C:15]([NH2:18])=[CH:16][CH:17]=1)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O>[C:11]([C:12]1[C:13]([NH2:19])=[N:14][C:15]([NH2:18])=[CH:16][CH:17]=1)#[CH:10]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 592554712,6-Pyridinediamine, 3-[2-(trimethylsilyl)ethynyl]-

Product 1

HCID 552816763-Ethynylpyridine-2,6-diamineYield 74.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of THF (100 mL) of 3-trimethylsilanylethynyl-pyridin-2,6-diamine (7.0 g) described in Manufacturing Example 4-2 was added tetrabutylammonium fluoride (1M THF solution, 17 mL) under ice cooling, 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, then concentrated under a reduced pressure, and the residue was purified by silica gel chromatography (ethyl acetate) to obtain the titled compound (3.4 g).

Workup

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

Sources & evidence

ORD record
ord-b3c6c09797a94148bcb969a3a1753ce3
Source dataset
uspto-grants-2012_05
Patent number
US08183264B2

Reaction notes

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