HCID 86689810, compound → HCID 86689811, compound

HRID 1396486Notes

Reaction equation

HRID 1396486 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([NH2:9])[CH:6]=[CH:5][C:4]=1[C:10]([CH3:12])=[CH2:11].[H][H]>CO.[Pd]>[CH:10]([C:4]1[CH:5]=[CH:6][C:7]([NH2:9])=[N:8][C:3]=1[O:2][CH3:1])([CH3:12])[CH3:11]

Participants

5

Reactant 2

HCID 86689810HCID 86689810, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86689811HCID 86689811, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 5-fluoro-6-isopropenyl-pyridin-2-ylamine (crude from Step 1, 8.47 mmol) in methanol (17.5 mL) was added 10% palladium on carbon (123 mg) at room temperature. A hydrogen balloon (1 atm) was attached and the mixture was stirred overnight. After 18 hours, the mixture was filtered over Celite, concentrated onto silica gel, and chromatographed (10% to 40% ethyl acetate in hexanes) to give 5-isopropyl-6-methoxypyridin-2-amine (740 mg, 53% over two steps). 1H NMR (400 MHz, CHLOROFORM-d6) δ ppm 7.26 (d, J=7.8 Hz, 1H), 6.07 (d, J=8.1 Hz, 1H), 4.19 (br. s, 2H), 3.90 (s, 3H), 3.08 (m, 1H), 1.17 (d, J=6.9 Hz, 6H).

Workup

  1. waitAfter 18 hours
  2. filtrationthe mixture was filtered over Celite
  3. concentrationconcentrated onto silica gel
  4. customchromatographed (10% to 40% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-6261115812d4470cbed67236e0f7a753
Source dataset
uspto-grants-2014_12
Patent number
US08901124B2

Reaction notes

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