Water → HCID 178482760, compound

HRID 1500994Notes

Reaction equation

HRID 1500994 reaction equation
[OH:1][C:2]1[C:7]([CH2:8][NH:9][C:10](=O)OC(C)(C)C)=[C:6]([CH3:17])[CH:5]=[C:4]([CH3:18])[N:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O>O1CCCC1.C(OCC)(=O)C>[CH3:17][C:6]1[CH:5]=[C:4]([CH3:18])[N:3]=[C:2]([OH:1])[C:7]=1[CH2:8][NH:9][CH3:10]

Participants

6

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 178425246HCID 178425246, compound

Product 1

HCID 178482760HCID 178482760, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of tert-butyl (2-hydroxy-4,6-dimethylpyridin-3-yl)methylcarbamate (700 mg, 2.78 mmol) in tetrahydrofuran (25 mL), lithium aluminum hydride (1 g, 26.3 mmol) was added in portions at room temperature. Then the mixture was heated at 70° C. for 15 hours with stirring. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate (20 mL). And then water (20 mL) was added to the reaction mixture dropwise. The organic phase was separated and concentrated to provide 4,6-dimethyl-3-((methylamino)methyl)pyridin-2-ol as a pale yellow solid (0.4 g, 87%). LRMS (M+H+) m/z: calcd 166.1. found 166.

Workup

  1. temperatureAfter cooling to room temperature
  2. customThe organic phase was separated
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-2e47daaedcf74fc58fd9e173e00c6d75
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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