Ammonia → 3-(aminomethyl)-4-(((tert-butyldimethylsilyl)oxy)methyl)-6-methylpyridin-2(1H)-one

HRID 1909339Notes

Reaction equation

HRID 1909339 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:15]=[C:14]([CH3:16])[NH:13][C:12](=[O:17])[C:11]=1[C:18]#[N:19])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].N>CO.[Ni]>[NH2:19][CH2:18][C:11]1[C:12](=[O:17])[NH:13][C:14]([CH3:16])=[CH:15][C:10]=1[CH2:9][O:8][Si:1]([C:4]([CH3:6])([CH3:5])[CH3:7])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 682948094-(((Tert-butyldimethylsilyl)oxy)methyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

Product 1

HCID 682947603-(aminomethyl)-4-(((tert-butyldimethylsilyl)oxy)methyl)-6-methylpyridin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-(((tert-butyldimethylsilyl)oxy)methyl)-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (3.8 g, 13.7 mmol) in methanol (200 mL), Raney Ni and ammonia (20 mL) were added and reaction stirred under hydrogen balloon pressure for 15 h. On completion, reaction mixture was filtered through a celite bed and the filtrate concentrated to obtain 3-(aminomethyl)-4-(((tert-butyldimethylsilyl)oxy)methyl)-6-methylpyridin-2(1H)-one as an off white solid (3.2 g, 83.1%).

Workup

  1. customreaction
  2. customOn completion, reaction mixture
  3. filtrationwas filtered through a celite bed
  4. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-54ff46429e0047b78caebc83b86f4456
Source dataset
uspto-grants-2013_12
Patent number
US08598167B1

Reaction notes

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