1,1'-Carbonyldiimidazole → N,N'-bis{[6-(tert-butyldimethylsilyloxy)methylpyridin-2-yl]methyl}urea

HRID 473231Notes

Reaction equation

HRID 473231 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])[N:4]=1.[C:18]([N:25]1[CH:29]=[CH:28][N:27]=[CH:26]1)(N1C=CN=C1)=[O:19]>C1COCC1>[Si:11]([O:10][CH2:9][C:5]1[N:4]=[C:3]([CH2:2][NH:1][C:18]([NH:25][CH2:29][C:28]2[CH:2]=[CH:3][CH:8]=[C:26]([CH2:9][O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])[N:27]=2)=[O:19])[CH:8]=[CH:7][CH:6]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:12])[CH3:13]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 668467232-Aminomethyl-6-[(tert-butyldimethylsilyloxy)methyl]pyridine

Product 1

HCID 67254702N,N'-bis{[6-(tert-butyldimethylsilyloxy)methylpyridin-2-yl]methyl}ureaYield 96.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Aminomethyl-6-[(tert-butyldimethylsilyloxy)methyl]pyridine (26) (380 mg, 1.50 mmol) and 1,1′-carbonyldiimidazole (150 mg, 0.92 mmol) were suspended in THF (10 mL). The air was evacuated from the reaction system, and then Ar was charged therein. The suspension was stirred for 24 hours at a room temperature. TLC was used to confirm there was no starting material in the mixture. Then, the reaction mixture was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (CDCl3:MeOH=50:1) to give N,N′-bis{[6-(tert-butyldimethylsilyloxy)methylpyridin-2-yl]methyl}urea (27) (384 mg, 96%) as yellow crystals.

Workup

  1. customThe air was evacuated from the reaction system
  2. additionAr was charged
  3. customThen, the reaction mixture was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (CDCl3:MeOH=50:1)

Sources & evidence

ORD record
ord-c166e049a18e491197888d7ada3e3030
Source dataset
uspto-grants-2014_01
Patent number
US08633304B2

Reaction notes

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