HCID 10248693, compound → 3-Amino-6-methyl-1-(tert-butoxycarbonylmethyl)-2-pyridinone

HRID 2228723Notes

Reaction equation

HRID 2228723 reaction equation
[C:1]([O:5][C:6](=[O:27])[CH2:7][N:8]1[C:13]([CH3:14])=[CH:12][CH:11]=[C:10]([NH:15]C(OCC2C=CC=CC=2)=O)[C:9]1=[O:26])([CH3:4])([CH3:3])[CH3:2]>C(OCC)(=O)C.[Pd]>[NH2:15][C:10]1[C:9](=[O:26])[N:8]([CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:27])[C:13]([CH3:14])=[CH:12][CH:11]=1

Participants

4

Reactant 1

HCID 10248693HCID 10248693, compound

Product 1

HCID 104901153-Amino-6-methyl-1-(tert-butoxycarbonylmethyl)-2-pyridinoneYield 99.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

ter-Butyl-2-[3-[(benzyloxy)carbonyl]amino-6-methyl-2-oxo-1(2H)-pyridinyl]acetate (preparation 4) (5 g, 13 mmol) was dissolved in ethyl acetate (70 ml), treated with 10% Pd on carbon catalyst (400 mg) and stirred under a hydrogen atmosphere (2 psi, room temperature, 3 hr). The catalyst was removed by filtration, and the solvent evaporated to dryness to give the desired product as a cream solid (3.08 g, 99%). 1H NMR (CDCl3) δ 1.40 (s, 9H), 2.20 (s, 3H), 4.00 (s, br, 2H), 4.70 (s, 2H), 5.90 (d, 1H), 6.45 (d, 1H). LRMS m/z=239.5 (M+1)+.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe solvent evaporated to dryness

Sources & evidence

ORD record
ord-99047f1ffc90455daa12d897c24a592a
Source dataset
uspto-grants-2002_07
Patent number
US06417203B1

Reaction notes

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