tert-Butyl methyl ether → (2-Methoxy-4,6-dimethylpyridin-3-yl)methanamine

HRID 577451Notes

Reaction equation

HRID 577451 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].CC(OC)(C)C.[CH3:13][O:14][C:15]1[C:20]([C:21]#[N:22])=[C:19]([CH3:23])[CH:18]=[C:17]([CH3:24])[N:16]=1>CC(OC)(C)C.C1COCC1>[CH3:13][O:14][C:15]1[C:20]([CH2:21][NH2:22])=[C:19]([CH3:23])[CH:18]=[C:17]([CH3:24])[N:16]=1

Participants

5

Reactant 3

HCID 15413tert-Butyl methyl etherHCID 5952762-Methoxy-4,6-dimethylnicotinonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 28064222(2-Methoxy-4,6-dimethylpyridin-3-yl)methanamine

Reagents, catalysts & solvents 1

HCID 22492792Mtbe thfSolvent

Procedure

LiAlH4 (48.0 g, 1.27 mol) was added into MTBE (600 mL) portion-wise at room temperature. To the suspension was added 2-methoxy-4,6-dimethylpyridine-3-carbonitrile (Cpd S, 103 g, 0.636 mol) in MTBE/THF (1:1, 600 mL) portion-wise. The reaction mixture was stirred at room temperature for an hour then quenched with water (75 mL). The precipitate was collected by filtration and the solids washed with THF (3×100 mL). The filtrate was concentrated under vacuum to give the 1-(2-methoxy-4,6-dimethylpyridin-3-yl)methanamine (Cpd T), which was used in the next step directly.

Workup

  1. customthen quenched with water (75 mL)
  2. filtrationThe precipitate was collected by filtration
  3. washthe solids washed with THF (3×100 mL)
  4. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-b59ef436e3ba4dde81607e9951c2a6d6
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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