Potassium Carbonate → Methyl 4-[(5-ethynyl-2-pyridyl)amino]-4-oxo-butanoate

HRID 525997Notes

Reaction equation

HRID 525997 reaction equation
[O:1]=[C:2]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]#[C:17][Si](C)(C)C)=[CH:12][N:11]=1)[CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6].C(=O)([O-])[O-].[K+].[K+]>CO>[C:16]([C:13]1[CH:14]=[CH:15][C:10]([NH:9][C:2](=[O:1])[CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6])=[N:11][CH:12]=1)#[CH:17]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 89444199Methyl 4-oxo-4-[[5-(2-trimethylsilylethynyl)-2-pyridyl]amino]butanoate

Product 1

HCID 89443928Methyl 4-[(5-ethynyl-2-pyridyl)amino]-4-oxo-butanoateYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 4-oxo-4-[[5-(2-trimethylsilylethynyl)-2-pyridyl]amino]butanoate (26 mg, 0.085 mmol) in methanol, potassium carbonate (5.90 mg, 0.042 mmol) is added in one portion and the reaction mixture is stirred at room temperature for 2 h. The reaction was stopped and the solution was partitioned between ethyl acetate and water. The aqueous layer was separated and extracted with ethyl acetate (2×). The combined organic layer was dried on magnesium sulfate and concentrated under vacuum to give methyl 4-[(5-ethynyl-2-pyridyl)amino]-4-oxo-butanoate A41 (12 mg, 60% yield). 1H NMR (400 MHz, CDCl3) 8.39 (d, 1H), 8.16 (m, 2H), 7.77 (d, 1H), 3.72 (s, 3H), 2.74 (m, 4H) ppm.

Workup

  1. customthe solution was partitioned between ethyl acetate and water
  2. customThe aqueous layer was separated
  3. extractionextracted with ethyl acetate (2×)
  4. customThe combined organic layer was dried on magnesium sulfate
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-511d2a41211c4fe792dc6bbe6036081d
Source dataset
uspto-grants-2016_05
Patent number
US09345244B2

Reaction notes

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