Methanol → 5-Ethynyl-6-methylpyridin-2-amine

HRID 1691301Notes

Reaction equation

HRID 1691301 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[C:9]#[C:10][Si](C)(C)C.CO.C(=O)([O-])[O-].[K+].[K+]>O>[C:9]([C:3]1[CH:4]=[CH:5][C:6]([NH2:8])=[N:7][C:2]=1[CH3:1])#[CH:10]

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 592552326-Methyl-5-trimethylsilanylethynyl-pyridin-2-ylamine

Product 1

HCID 552859385-Ethynyl-6-methylpyridin-2-amineYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 6-methyl-5-trimethylsilanylethynyl-pyridin-2-ylamine (450 mg, 1.9 mmol) described in Manufacturing Example 187-1-1 and methanol (5 mL) was added potassium carbonate (390 mg, 2.8 mmol), which was stirred for 30 minutes at the same temperature. Water was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, and was concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:1) to obtain the title compound (220 mg, 88%).

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium chloride
  3. concentrationwas concentrated under a reduced pressure
  4. customThe residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-e3250f0633cd4d54b5d38d9fca0efcc3
Source dataset
uspto-grants-2012_04
Patent number
US08153662B2

Reaction notes

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