Tert-butyl ((5-cyano-6-methoxy-4-methylpyridin-2-yl)methyl)carbamate → Tert-butyl ((5-(aminomethyl)-6-methoxy-4-methylpyridin-2-yl)methyl)carbamate

HRID 42499Notes

Reaction equation

HRID 42499 reaction equation
[C:1]([O:5][C:6](=[O:20])[NH:7][CH2:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([C:16]#[N:17])=[C:11]([O:18][CH3:19])[N:10]=1)([CH3:4])([CH3:3])[CH3:2]>CC(O)=O.C(O)C.[Ni]>[C:1]([O:5][C:6](=[O:20])[NH:7][CH2:8][C:9]1[CH:14]=[C:13]([CH3:15])[C:12]([CH2:16][NH2:17])=[C:11]([O:18][CH3:19])[N:10]=1)([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 1

HCID 86696542Tert-butyl ((5-cyano-6-methoxy-4-methylpyridin-2-yl)methyl)carbamate

Product 1

HCID 67951653Tert-butyl ((5-(aminomethyl)-6-methoxy-4-methylpyridin-2-yl)methyl)carbamateYield 88%

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

A clear solution of tert-butyl((5-cyano-6-methoxy-4-methylpyridin-2-yl)methyl)carbamate (0.65 g, 2.344 mmol) in HOAc (5 mL) and Ethanol (20 mL) was treated on an H-Cube apparatus (50 psi, 40° C., 1 mL/min., Raney Nickel cartridge) for 18 hr overnight. LCMS showed that the reaction was complete. The reaction was evaporated to dryness under vacuum. Purified by silica gel chromatography (Analogix, SF25-60 g, 0 to 10% (5% NH4OH/MeOH) in CH2Cl2). The pure fractions were combined and evaporated to dryness under vacuum to give the product tert-butyl((5-(aminomethyl)-6-methoxy-4-methylpyridin-2-yl)methyl)carbamate (0.58 g, 2.061 mmol, 88% yield) as a clear thick oil.

Workup

  1. customThe reaction was evaporated to dryness under vacuum
  2. customPurified by silica gel chromatography (Analogix
  3. customevaporated to dryness under vacuum

Sources & evidence

ORD record
ord-f6e68028a2e047869aa1f7c55ad51a00
Source dataset
uspto-grants-2013_09
Patent number
US08536179B2

Reaction notes

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