6-Methyl-2-pyridylmethanol → (6-Methylpyridin-2-yl)methanamine

HRID 2070983Notes

Reaction equation

HRID 2070983 reaction equation
[C:1]1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[N:18]12CCC[N:25]=[C:24]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2.CC1N=C(CO)C=CC=1>C1(C)C=CC=CC=1.CO.[OH-].[OH-].[Pd+2]>[CH3:1][C:24]1[N:25]=[C:20]([CH2:19][NH2:18])[CH:21]=[CH:22][CH:23]=1

Participants

7

Reactant 3

HCID 707366-Methyl-2-pyridylmethanolHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 246721(6-Methylpyridin-2-yl)methanamineYield 119.1%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

Diphenylphosphoryl azide (DPPA) (0.74 mL, 0.9 g, 3.4 mmol, 1.2 eq) and 1,8-Diazabicyclo(5.4.0)undec-7-ene (DBU) (0.508 mL, 0.52 g, 3.4 mmol, 1.2 eq) were added to a stirred solution of the (6-methylpyridin-2-yl)methanol (0.35 g, 2.8 mmol, 1 eq) in 7 mL anh. toluene under Ar. After stirring overnight, the solvent was removed in vacuo. Purification via flash chromatography yielded 0.47 g (3.2 mmol, 113% yield of the crude product. The crude was dissolved in 5 mL MeOH. Pd(OH)2 (20% by wt. on carbon, 0.040 g) was added, and the mixture was stirred vigorously under H2 overnight. The mixture was filtered through Celite, and the filter cake rinsed with MeOH. The solvent was removed in vacuo yielding 0.4948 g of crude (6-methylpyridin-2-yl)methanamine.

Workup

  1. customthe solvent was removed in vacuo
  2. customPurification via flash chromatography
  3. customyielded 0.47 g (3.2 mmol, 113% yield of the crude product
  4. stirringthe mixture was stirred vigorously under H2 overnight
  5. filtrationThe mixture was filtered through Celite
  6. washthe filter cake rinsed with MeOH
  7. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-d2ab17ad9c2d4c84b8adb11286b65084
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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