N-[3-(4,4'-dimethoxytrityloxymethyl)benzyl]-N'-{[6-(tert-butyldimethylsilyloxymethyl)pyridin-2-yl]methyl}thiourea → N-[3-(4,4'-dimethoxytrityloxymethyl)benzyl]-N'-[(6-hydroxymethylpyridin-2-yl)methyl]thiourea

HRID 473230Notes

Reaction equation

HRID 473230 reaction equation
[CH3:1][O:2][C:3]1[CH:52]=[CH:51][C:6]([C:7]([O:22][CH2:23][C:24]2[CH:25]=[C:26]([CH:48]=[CH:49][CH:50]=2)[CH2:27][NH:28][C:29]([NH:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([CH2:39][O:40][Si](C(C)(C)C)(C)C)[N:34]=2)=[S:30])([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1>C1COCC1>[CH3:15][O:14][C:11]1[CH:10]=[CH:9][C:8]([C:7]([O:22][CH2:23][C:24]2[CH:25]=[C:26]([CH:48]=[CH:49][CH:50]=2)[CH2:27][NH:28][C:29]([NH:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([CH2:39][OH:40])[N:34]=2)=[S:30])([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:52][CH:51]=2)=[CH:13][CH:12]=1

Participants

3

Reactant 1

HCID 87326894N-[3-(4,4'-dimethoxytrityloxymethyl)benzyl]-N'-{[6-(tert-butyldimethylsilyloxymethyl)pyridin-2-yl]methyl}thiourea

Product 1

HCID 86671516N-[3-(4,4'-dimethoxytrityloxymethyl)benzyl]-N'-[(6-hydroxymethylpyridin-2-yl)methyl]thioureaYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-[3-(4,4′-Dimethoxytrityloxymethyl)benzyl]-N′-{[6-(tert-butyldimethylsilyloxymethyl)pyridin-2-yl]methyl}thiourea (22) (316 mg, 0.43 mmol) was suspended in THF (2.2 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 1.0M TBAF in THF (0.48 mL). The mixture was further stirred for 12 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 purified by silica gel column chromatography (CDCl3:MeOH=200:1 to 50:1) to give N-[3-(4,4′-dimethoxytrityloxymethyl)benzyl]-N′-[(6-hydroxymethylpyridin-2-yl)methyl]thiourea (13) (141 mg, 54%) as yellow crystals.

Workup

  1. customThe air was evacuated from the reaction system
  2. additionAr was charged
  3. additionTo the suspension was added 1.0M TBAF in THF (0.48 mL)
  4. stirringThe mixture was further stirred for 12 hours
  5. customThen, the reaction mixture was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (CDCl3:MeOH=200:1 to 50:1)

Sources & evidence

ORD record
ord-2d931c9a2d0c412cb20b843750240ea3
Source dataset
uspto-grants-2014_01
Patent number
US08633304B2

Reaction notes

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