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

HRID 473232ノート

反応式

HRID 473232 の反応式
[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

参加物

3

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-693c8ccf96424ac5b7f86a855f665b2a
出典データセット
uspto-grants-2014_01
特許番号
US08633304B2

反応ノート

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