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

HRID 473232노트

반응식

HRID 473232 반응식
[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

참가 물질

3

반응물 1

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-693c8ccf96424ac5b7f86a855f665b2a
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633304B2

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