Tetrabutylammonium Fluoride → N-[3-(4,4'-dimethoxytrityloxymethyl)benzyl]-N'-[(6-hydroxymethylpyridin-2-yl)methyl]urea

HRID 473227Notes

Reaction equation

HRID 473227 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)=[O: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.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>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)=[O: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

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67255922N-[3-(4,4'-dimethoxytrityloxymethyl)benzyl]-N'-{[6-(tert-butyldimethylsilyloxy)methylpyridin-2-yl]methyl}urea

Product 1

HCID 68312911N-[3-(4,4'-dimethoxytrityloxymethyl)benzyl]-N'-[(6-hydroxymethylpyridin-2-yl)methyl]ureaYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of N-[3-(4,4′-dimethoxytrityloxymethyl)benzyl]-N′-{[6-(tert-butyldimethylsilyloxy)methylpyridin-2-yl]methyl}urea (6) (410 mg, 0.57 mmol) in THF (2.2 mL), which was stirred, was added dropwise a solution of 1.0M TBAF in THF (0.64 mL), and stirred for 4 hours at a room temperature under Ar atmosphere. TLC was used to confirm there was no starting material in the reaction mixture. Then, the reaction mixture was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (CHCl3:MeOH=20:1) to give N-[3-(4,4′-dimethoxytrityloxymethyl)benzyl]-N′-[(6-hydroxymethylpyridin-2-yl)methyl]urea (7) (336 mg, 98%) as colorless crystals.

Workup

  1. stirringstirred for 4 hours at a room temperature under Ar atmosphere
  2. customThen, the reaction mixture was evaporated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (CHCl3:MeOH=20:1)

Sources & evidence

ORD record
ord-e168f372f1384990a1442d7268e84924
Source dataset
uspto-grants-2014_01
Patent number
US08633304B2

Reaction notes

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