2-Aminopyridine → 2-(Boc-amino)pyridine

HRID 1930756Notes

Reaction equation

HRID 1930756 reaction equation
C(O[C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])(C)(C)C.[NH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1>C(O)(C)(C)C>[C:8]([O:7][C:6](=[O:12])[NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)([CH3:9])([CH3:10])[CH3:11]

Participants

4

Reactant 2

HCID 104392-AminopyridineHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

Product 1

HCID 112063492-(Boc-amino)pyridineYield 92.8%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To a solution of tert-butyl alcohol (650 mL) and di-tert-butylcarbonate (24 g) was added 2-aminopyridine (9.4 g) slowly. This mixture was stirred at room temperature for 24 hours. The reaction solution was concentrated under a reduced pressure, and the residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:1) to obtain the title compound (18 g).

Workup

  1. concentrationThe reaction solution was concentrated under a reduced pressure
  2. customthe residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-8c1753f44cda4391a6c8b5a422c6585b
Source dataset
uspto-grants-2012_05
Patent number
US08188119B2

Reaction notes

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