4-Aminopyridine → 4-(2,2,2-Trimethylacetamido)pyridine

HRID 731596Notes

Reaction equation

HRID 731596 reaction equation
[C:1](Cl)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[NH2:8][C:9]1[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:3][C:2]([CH3:5])([CH3:4])[C:1]([NH:8][C:9]1[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=1)=[O:6]

Participants

5

Reactant 3

HCID 17274-AminopyridineHCID 8471TriethylamineHCID 62493Pivaloyl chloride

Product 1

HCID 4270594-(2,2,2-Trimethylacetamido)pyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of pivaloyl chloride (1.1 eq.) in CH2Cl2 is added to a solution of 4-aminopyridine (1 eq.) and triethylamine (1.2 eq.) in CH2Cl2, stirred at 0° C. for 2 h, washed with aqueous sodium bicarbonate, dried over MgSO4 and concentrated in vacuo. The resultant residue is purified by flash chromatography over silica gel to afford the title propionamide compound.

Workup

  1. washwashed with aqueous sodium bicarbonate
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe resultant residue is purified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-95bc10cbfd334048859bbeb940f816fb
Source dataset
uspto-grants-2009_09
Patent number
US07585876B2

Reaction notes

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