Triethylamine → tert-Butyl (6-methoxypyridin-3-yl)carbamate

HRID 1925332Notes

Reaction equation

HRID 1925332 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.C(N(CC)CC)C.[C:17](=O)([O:23]C(C)(C)C)[O:18][C:19]([CH3:22])([CH3:21])[CH3:20]>O1CCOCC1>[CH3:9][O:8][C:5]1[N:6]=[CH:7][C:2]([NH:1][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 811216-Methoxy-3-pyridinylamineHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

Product 1

HCID 2763103tert-Butyl (6-methoxypyridin-3-yl)carbamate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a stirring solution of 5-amino-2-methoxypyridine (8.00 g, 64.4 mmol) and triethylamine (11.7 mL, 83.8 mmol) in dioxane (32 mL) at 0° C. was added a solution of di-tert-butyl carbonate in dioxane (20 mL). The reaction mixture was allowed to warm to RT, stirred for 16 h. After concentration in vacuo, the residue was dissolved in 65 mL of EtOAc and 32 mL of a saturated aqueous NaHCO3 solution and stirred at RT for 2 h. The layers were separated. The organic layer was washed with water and dried over Na2SO4, filtered and concentrated in vacuo to provide the title compound.

Workup

  1. concentrationAfter concentration in vacuo
  2. dissolutionthe residue was dissolved in 65 mL of EtOAc
  3. stirring32 mL of a saturated aqueous NaHCO3 solution and stirred at RT for 2 h
  4. customThe layers were separated
  5. washThe organic layer was washed with water
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-09b049bb4a8840c7b1c2042414b9caaa
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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