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

HRID 1891237Notes

Reaction equation

HRID 1891237 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.[C:21]([Si:25](Cl)([CH3:27])[CH3:26])([CH3:24])([CH3:23])[CH3:22]>O1CCCC1>[Si:25]([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:21]([CH3:24])([CH3:23])[CH3:22])([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 44232377[3-(6-Aminopyridin-3-yl)phenyl]methanol

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-butylchlorodimethylsilane, and the mixture is left to stir at ambient temperature for 48 hours. The reaction mixture is then hydrolyzed with water and the organic phase, 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. extractionhydrolyzed with water and the organic phase, 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-023e5f5af04642eda3bd63ea061dc2ab
Source dataset
uspto-grants-2013_08
Patent number
US08507520B2

Reaction notes

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