5-Fluoro-4-isopropyl-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile → 3-(Aminomethyl)-5-fluoro-4-isopropyl-6-methylpyridin-2(1H)-one

HRID 2208659Notes

Reaction equation

HRID 2208659 reaction equation
[F:1][C:2]1[C:3]([CH:12]([CH3:14])[CH3:13])=[C:4]([C:10]#[N:11])[C:5](=[O:9])[NH:6][C:7]=1[CH3:8]>CO.[Ni]>[NH2:11][CH2:10][C:4]1[C:5](=[O:9])[NH:6][C:7]([CH3:8])=[C:2]([F:1])[C:3]=1[CH:12]([CH3:14])[CH3:13]

Participants

4

Reactant 1

HCID 866848985-Fluoro-4-isopropyl-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile

Product 1

HCID 866848973-(Aminomethyl)-5-fluoro-4-isopropyl-6-methylpyridin-2(1H)-oneYield 90%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

5-Fluoro-4-isopropyl-6-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (100 mg, 0.515 mmol) in 100 mL flask was dissolved in a mixture of MeOH (6 mL) and 2 mL NH3aq (2 mL, 25%). Reduction was conducted using H-Cube with Raney-Ni as a catalyst at room temperature for 3-4 h. On completion of reaction (monitored by TLC), reaction was concentrated under reduced pressure to afford titled compound as a grey solid (90 mg, 90%). 1H NMR (400 MHz, CD3OD) δ ppm 4.04 (s, 2H), 3.22 (m, 1H), 2.24 (d, J=3.4 Hz, 3H), 1.32 (dd, J=7.0, 1.8 Hz, 6H); LCMS E-S (M+H)=199.2.

Workup

  1. customat room temperature
  2. customfor 3-4 h
  3. customOn completion of reaction (monitored by TLC), reaction
  4. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-4e26f7dde75f47f3ada6cdd265dec6cf
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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