Imidazole → 5-[3-(tert-Butyldimethylsilanyloxymethyl)phenyl]pyridin-2-ylamine

HRID 2196452Notes

Reaction equation

HRID 2196452 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([CH2:14][OH:15])[CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.N1C=CN=C1.[Cl-].[C:22]([SiH:26]([CH3:28])[CH3:27])([CH3:25])([CH3:24])[CH3:23]>O1CCCC1>[Si:26]([O:15][CH2:14][C:10]1[CH:9]=[C:8]([C:5]2[CH:4]=[CH:3][C:2]([NH2:1])=[N:7][CH:6]=2)[CH:13]=[CH:12][CH:11]=1)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:28])[CH3:27]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 44232377[3-(6-Aminopyridin-3-yl)phenyl]methanolHCID 131722836Tert-butyldimethylsilane chloride

Product 1

HCID 442323785-[3-(tert-Butyldimethylsilanyloxymethyl)phenyl]pyridin-2-ylamineYield 89.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4.99 g of [3-(6-aminopyridin-3-yl)phenyl]methanol are placed in a round-bottomed flask and dissolved in 240 ml of tetrahydrofuran. 2.2 g of 1H-imidazole are added thereto, followed by 4.51 g of tert-butyldimethylsilane chloride, and the mixture is left to stir at ambient temperature for 48 hours. The reaction mixture is then hydrolysed with water, and the organic phase, which has been extracted with ethyl acetate, is separated, dried over magnesium sulphate and concentrated under reduced pressure. The residue obtained is purified by silica gel chromatography, elution being carried out with a heptane/ethyl acetate mixture. 7.0 g of compound are obtained.

Workup

  1. waitthe mixture is left
  2. extractionhydrolysed with water, and the organic phase, which has been extracted with ethyl acetate
  3. customis separated
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue obtained
  7. customis purified by silica gel chromatography, elution

Sources & evidence

ORD record
ord-f9556880a3d8426c89bfce34dc9eb02a
Source dataset
uspto-grants-2012_12
Patent number
US08338451B2

Reaction notes

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