Methanol → 5-Ethynylpyridin-2-amine

HRID 77854Notes

Reaction equation

HRID 77854 reaction equation
C[Si]([C:5]#[C:6][C:7]1[CH:8]=[CH:9][C:10]([NH2:13])=[N:11][CH:12]=1)(C)C.CO.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[C:6]([C:7]1[CH:8]=[CH:9][C:10]([NH2:13])=[N:11][CH:12]=1)#[CH:5]

Participants

5

Reactant 3

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

Product 1

HCID 219548275-Ethynylpyridin-2-amineYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-trimethylsilanylethynyl-pyridin-2-ylamine (26 mg, 137 mmol) described in Manufacturing Example 28-1-2 in tetrahydrofuran (1 mL) and methanol (1 mL) was added potassium carbonate (37.9 mg, 274 mmol) at room temperature, which was stirred for 1 hour at room temperature. The reaction solution was partitioned into water and ethyl acetate at 0° C. The organic layer was washed with saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was concentrated under a reduced pressure. The residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=1:1) to obtain the title compound (16 mg, 99%).

Workup

  1. customThe reaction solution was partitioned into water and ethyl acetate at 0° C
  2. washThe organic layer was washed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationthe solvent was concentrated under a reduced pressure
  5. customThe residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-6a43d2ee26304e1db26883df77080a70
Source dataset
uspto-grants-2014_09
Patent number
US08841327B2

Reaction notes

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