Imidazole → 2-Aminomethyl-6-[(tert-butyldimethylsilyloxy)methyl]pyridine

HRID 254173Notes

Reaction equation

HRID 254173 reaction equation
[NH2:1][CH2:2][C:3]1[N:8]=[C:7]([CH2:9][OH:10])[CH:6]=[CH:5][CH:4]=1.[Si:11](Cl)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].N1C=CN=C1.[OH-].[Na+]>CN(C=O)C>[Si:11]([O:10][CH2:9][C:7]1[N:8]=[C:3]([CH2:2][NH2:1])[CH:4]=[CH:5][CH:6]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 14798Sodium HydroxideHCID 28928tert-Butyldimethylsilyl chlorideHCID 21076956(6-(Aminomethyl)pyridin-2-yl)methanol

Product 1

HCID 668467232-Aminomethyl-6-[(tert-butyldimethylsilyloxy)methyl]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6-aminomethypyridine-2-methanol (5 g, 36.2 mmol) in anhydrous DMF (25 mL) at 0° C. was treated with tert-butyldimethylsilyl chloride (5.728 g, 38 mmol) and imidazole (2.584 g, 38 mmol), stirred at room temperature for 20 h, poured into 1.5-M aqueous NaOH (100 mL) and extracted with EtOAc (3×20 mL). The combined organic phase was washed with water (4×10 mL), brine (2×20 mL), dried (MgSO4) and concentrated in vacuo to give the title compound as a yellow oil; NMR δH (400 MHz, CDCl3) 0.82 (9H, s), 0.87 (6H, s), 1.81 (2H, s), 3.84 (2H, s), 4.73 (2H, s), 7.03 (1H, d, J 8.0 Hz), 7.28 (1H, d, J 7.5 Hz) and 7.57 (1H, t, J 8.0 Hz); M/Z 253 (M+H)+

Workup

  1. extractionextracted with EtOAc (3×20 mL)
  2. washThe combined organic phase was washed with water (4×10 mL), brine (2×20 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8c4e06f5c4f04d75b6bcff965c2d6304
Source dataset
uspto-grants-2011_01
Patent number
US07875600B2

Reaction notes

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