Methanol → 5-Ethynylpyridin-2-amine

HRID 1927215Notes

Reaction equation

HRID 1927215 reaction equation
C1COCC1.CO.C[Si]([C:12]#[C:13][C:14]1[CH:15]=[CH:16][C:17]([NH2:20])=[N:18][CH:19]=1)(C)C.C(=O)([O-])[O-].[K+].[K+]>O>[C:13]([C:14]1[CH:15]=[CH:16][C:17]([NH2:20])=[N:18][CH:19]=1)#[CH:12]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 224828585-(2-(Trimethylsilyl)ethynyl)pyridin-2-amine

Product 1

HCID 219548275-Ethynylpyridin-2-amineYield 99.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of THF (1 mL) and methanol (1 mL) of 5-trimethylsilanylethynyl-pyridin-2-ylamine (26 mg) described in Manufacturing Example 3-2 was added potassium carbonate (38 mg) at room temperature, which was stirred for 1 hour at room temperature. Water was added at 0° C. to the reaction solution, which was then extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered, after which the solvent was evaporated from the filtrate under a reduced pressure. The residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=1:1) to obtain the titled compound (16 mg).

Workup

  1. extractionwas then extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customafter which the solvent was evaporated from the filtrate under a reduced pressure
  6. customThe residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-cb77dafaf87c48c5bb543e6459916674
Source dataset
uspto-grants-2012_05
Patent number
US08183264B2

Reaction notes

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