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

HRID 473232Notes

Reaction equation

HRID 473232 reaction equation
[Si]([O:8][CH2:9][C:10]1[N:15]=[C:14]([CH2:16][NH:17][C:18]([NH:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][O:29][Si](C(C)(C)C)(C)C)[N:23]=2)=[O:19])[CH:13]=[CH:12][CH:11]=1)(C(C)(C)C)(C)C>C1COCC1>[OH:29][CH2:28][C:24]1[N:23]=[C:22]([CH2:21][NH:20][C:18]([NH:17][CH2:16][C:14]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:9][OH:8])[N:15]=2)=[O:19])[CH:27]=[CH:26][CH:25]=1

Participants

3

Reactant 1

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

Product 1

HCID 67256715N,N'-Bis{[6-(hydroxymethyl)pyridin-2-yl]methyl}ureaYield 166.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N,N′-Bis{[6-(tert-butyldimethylsilyloxy)methylpyridin-2-yl]methyl}urea (27) (855 mg, 1.61 mmol) was suspended in THF (8.1 mL). The air was evacuated from the reaction system, and then Ar was charged therein. The suspension was stirred at a room temperature. To the suspension was added dropwise 1.0M TBAF in THF (3.7 mL), and further stirred for 5 hours. 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 suction-filtered to give N,N′-bis{[6-(hydroxymethyl)pyridin-2-yl]methyl}urea (28) (812 mg) as white crystals.

Workup

  1. customThe air was evacuated from the reaction system
  2. additionAr was charged
  3. additionTo the suspension was added dropwise 1.0M TBAF in THF (3.7 mL)
  4. stirringfurther stirred for 5 hours
  5. customThen, the reaction mixture was evaporated under reduced pressure
  6. filtrationThe residue was suction-filtered

Sources & evidence

ORD record
ord-693c8ccf96424ac5b7f86a855f665b2a
Source dataset
uspto-grants-2014_01
Patent number
US08633304B2

Reaction notes

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