4-{[(2-chloro-5,6-dimethyl-3-nitropyridin-4-yl)amino]methyl}tetrahydro-2H-pyran-4-ol → 4-{[(3-amino-2-chloro-5,6-dimethylpyridin-4-yl)amino]methyl}tetrahydro-2H-pyran-4-ol

HRID 1469309Notes

Reaction equation

HRID 1469309 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[C:6]([NH:11][CH2:12][C:13]2([OH:19])[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:5]([CH3:20])=[C:4]([CH3:21])[N:3]=1>[Pt].C(OCC)(=O)C>[NH2:8][C:7]1[C:2]([Cl:1])=[N:3][C:4]([CH3:21])=[C:5]([CH3:20])[C:6]=1[NH:11][CH2:12][C:13]1([OH:19])[CH2:14][CH2:15][O:16][CH2:17][CH2:18]1

Participants

4

Reactant 1

HCID 575155234-{[(2-chloro-5,6-dimethyl-3-nitropyridin-4-yl)amino]methyl}tetrahydro-2H-pyran-4-ol

Product 1

HCID 575155244-{[(3-amino-2-chloro-5,6-dimethylpyridin-4-yl)amino]methyl}tetrahydro-2H-pyran-4-ol

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

4-{[(2-Chloro-5,6-dimethyl-3-nitropyridin-4-yl)amino]methyl}tetrahydro-2H-pyran-4-ol (8.74 g, 27.7 mmol), 10% platinum on carbon (874 mg), and ethyl acetate (185 mL) were combined and placed under hydrogen pressure (50 psi, 3.4×105 Pa) on a Parr apparatus for 4 hours. The reaction mixture was filtered through a layer of CELITE filter aid and the filter cake was washed with 1:1 ethyl acetate:methanol. The filtrate was concentrated under reduced pressure to provide crude 4-{[(3-amino-2-chloro-5,6-dimethylpyridin-4-yl)amino]methyl}tetrahydro-2H-pyran-4-ol.

Workup

  1. customfor 4 hours
  2. filtrationThe reaction mixture was filtered through a layer of CELITE
  3. filtrationfilter aid
  4. washthe filter cake was washed with 1:1 ethyl acetate
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0a7080e12b9a4524bdc4a6536bb0ec48
Source dataset
uspto-grants-2015_04
Patent number
US09006264B2

Reaction notes

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