tert-Butyl 5-cyano-6-methylpyridin-2-ylcarbamate → tert-Butyl 5-(aminomethyl)-6-methylpyridin-2-ylcarbamate

HRID 361372Notes

Reaction equation

HRID 361372 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[C:11]([CH3:17])[N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)(=O)C.[Pd]>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][NH2:16])=[C:11]([CH3:17])[N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 10704790tert-Butyl 5-cyano-6-methylpyridin-2-ylcarbamate

Product 1

HCID 10681361tert-Butyl 5-(aminomethyl)-6-methylpyridin-2-ylcarbamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 2-t-butoxycarbonylamino-5-cyano-6-methylpyridine (14.68 g, 62.9 mmol) and 10% Pd/C (1.5 g) in glacial acetic acid (150 ml) was shaken on a Parr apparatus at 60 psi for 88 h. The reaction was filtered through celite and was evaporated in vacuo. The residue was dissolved in water and the solution was washed with methylene chloride (2 times), then was basified with sodium carbonate and extracted with ethyl acetate (2 times). The combined ethyl acetate layers were dried (Na2SO4) and evaporated in vacuo to a solid. The crude product was recrystallized (ethyl acetate/hexanes) to give the title compound:

Workup

  1. filtrationThe reaction was filtered through celite
  2. customwas evaporated in vacuo
  3. dissolutionThe residue was dissolved in water
  4. washthe solution was washed with methylene chloride (2 times)
  5. extractionextracted with ethyl acetate (2 times)
  6. dry with materialThe combined ethyl acetate layers were dried (Na2SO4)
  7. customevaporated in vacuo to a solid
  8. customThe crude product was recrystallized (ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-011006007f4e4d169fe762ec52a49e09
Source dataset
uspto-grants-1999_02
Patent number
US05866573

Reaction notes

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