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Triethylamine → N-[2-(tert-butyldimethylsilyloxy)ethyl]-N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]amine

HRID 2303356
Notes
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Reaction equation

HRID 2303356 reaction equation
[OH:1][CH2:2][CH2:3][NH:4][CH2:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([C:12]2[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=2)[CH:7]=1.C(N(CC)CC)C.[C:31]([Si:35](Cl)([CH3:37])[CH3:36])([CH3:34])([CH3:33])[CH3:32]>C(#N)C.CN(C)C1C=CN=CC=1>[Si:35]([O:1][CH2:2][CH2:3][NH:4][CH2:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([C:12]2[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=2)[CH:7]=1)([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:37])[CH3:36]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 18460604N-(2-Hydroxyethyl)-N-[[2-(3,4,5-trimethoxyphenyl)-pyridin-4-yl]methyl]amine

Product 1

HCID 18460594N-[2-(tert-butyldimethylsilyloxy)ethyl]-N-[[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl]amine

Reagents, catalysts & solvents 2

HCID 14284
4-(Dimethylamino)pyridine
Catalyst
HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

N-(2-Hydroxyethyl)-N-[[2-(3,4,5-trimethoxyphenyl)-pyridin-4-yl]methyl]amine (5.0 g) was dissolved in acetonitrile (100 mL), and to the solution triethylamine (2.22 g) and 4-(dimethylamino)pyridine (250 mg) were added, and tert-butylchlorodimethylsilane (3.08 g) was then added. The mixture was stirred at 50° C. for 4 hours. The reaction, the reaction mixture was concentrated under reduced pressure, ethyl acetate was added to the residue, and the mixture was washed with water and saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (chloroform:methanol=30:1) to obtain the title compound.

Workup

  1. customThe reaction
  2. concentrationthe reaction mixture was concentrated under reduced pressure, ethyl acetate
  3. additionwas added to the residue
  4. washthe mixture was washed with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel (chloroform:methanol=30:1)

Sources & evidence

ORD record
ord-78b1302bcf634701833b5eba05675481
Source dataset
uspto-grants-2002_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06432957B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes