Methanol → Tert-butyl (5-ethynylpyridin-3-yl)carbamate

HRID 1614979Notes

Reaction equation

HRID 1614979 reaction equation
C[Si]([C:5]#[C:6][C:7]1[CH:8]=[C:9]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH:10]=[N:11][CH:12]=1)(C)C.CO.C(=O)([O-])[O-].[K+].[K+]>O>[C:6]([C:7]1[CH:8]=[C:9]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:18])([CH3:17])[CH3:19])[CH:10]=[N:11][CH:12]=1)#[CH:5]

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 57962266tert-Butyl {5-[(trimethylsilyl)ethynyl]pyridin-3-yl}carbamate

Product 1

HCID 57962286Tert-butyl (5-ethynylpyridin-3-yl)carbamateYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a reaction flask were added tert-butyl {5-[(trimethylsilyl)ethynyl]pyridin-3-yl}carbamate (2.0 g, 6.9 mmol), methanol (25 mL), and a solution of potassium carbonate (7.1 g, 52 mmol) in water (25 mL). The reaction mixture was stirred at rt overnight. The solvent was removed under vacuum and the residue was diluted with EtOAc and water. After separation, the organic layer was dried over Na2SO4 and concentrated under vacuum. The crude product was purified by silica gel column chromatography to give the desired product as a white powder (1.0 g, 67%). LCMS for C12H15N2O2 (M+H)+: m/z=219.0.

Workup

  1. customThe solvent was removed under vacuum
  2. additionthe residue was diluted with EtOAc and water
  3. customAfter separation
  4. dry with materialthe organic layer was dried over Na2SO4
  5. concentrationconcentrated under vacuum
  6. customThe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-7477068ec7834bd8a8269f1dd67d398e
Source dataset
uspto-grants-2014_07
Patent number
US08765727B2

Reaction notes

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