Tetrahydrofuran → (2-Amino-6-methylpyridin-3-yl)methanol

HRID 1691283Notes

Reaction equation

HRID 1691283 reaction equation
O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:14][C:15](=O)[C:16]1[CH:21]=[CH:20][C:19]([CH3:22])=[N:18][C:17]=1[NH2:23])C.[OH-].[Na+]>O>[NH2:23][C:17]1[C:16]([CH2:15][OH:14])=[CH:21][CH:20]=[C:19]([CH3:22])[N:18]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 12494686Ethyl 2-amino-6-methylnicotinateHCID 21226445Aluminium lithium hydride

Product 1

HCID 55281422(2-Amino-6-methylpyridin-3-yl)methanolYield 74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a tetrahydrofuran (12 mL) solution of lithium aluminum hydride (706 mg, 14.9 mmol, purity: 80%) was added 2-amino-6-methyl-nicotinic acid ethyl ester (670 mg, 3.72 mmol) described in Manufacturing Example 170-1-2 at 0° C., which was stirred for 30 minutes at room temperature. Water (706 μL), a 5 N sodium hydroxide aqueous solution (706 μL), and water (2.12 mL) were added to the reaction mixture in that order at 0° C., which was filtered through a Celite pad. The filtrate was concentrated under a reduced pressure, and the residue was purified by NH silica gel column chromatography (ethyl acetate:methanol=10:1) to obtain the title compound (379 mg, 74%).

Workup

  1. customdescribed in Manufacturing Example 170-1-2 at 0° C.
  2. filtrationwhich was filtered through a Celite pad
  3. concentrationThe filtrate was concentrated under a reduced pressure
  4. customthe residue was purified by NH silica gel column chromatography (ethyl acetate:methanol=10:1)

Sources & evidence

ORD record
ord-cf6bb47629fc441d8b1daf75240cc21b
Source dataset
uspto-grants-2012_04
Patent number
US08153662B2

Reaction notes

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