1,1'-Carbonyldiimidazole → N-[3-(4,4'-dimethoxytrityloxymethyl)benzyl]-N'-{[6-(tert-butyldimethylsilyloxy)methylpyridin-2-yl]methyl}urea

HRID 473226Notes

Reaction equation

HRID 473226 reaction equation
[CH3:1][O:2][C:3]1[CH:33]=[CH:32][C:6]([C:7]([O:22][CH2:23][C:24]2[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=2)[CH2:27][NH2:28])([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.[C:34](N1C=CN=C1)(N1C=CN=C1)=[O:35].[NH2:46][CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[C:50]([CH2:54][O:55][Si:56]([C:59]([CH3:62])([CH3:61])[CH3:60])([CH3:58])[CH3:57])[N:49]=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:29]=[CH:30][CH:31]=2)[CH2:27][NH:28][C:34]([NH:46][CH2:47][C:48]2[CH:53]=[CH:52][CH:51]=[C:50]([CH2:54][O:55][Si:56]([C:59]([CH3:62])([CH3:61])[CH3:60])([CH3:57])[CH3:58])[N:49]=2)=[O:35])([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:33][CH:32]=2)=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 668467232-Aminomethyl-6-[(tert-butyldimethylsilyloxy)methyl]pyridineHCID 672534783-(4,4'-Dimethoxytrityloxymethyl)benzylamine

Product 1

HCID 67255922N-[3-(4,4'-dimethoxytrityloxymethyl)benzyl]-N'-{[6-(tert-butyldimethylsilyloxy)methylpyridin-2-yl]methyl}ureaYield 54.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 3-(4,4′-dimethoxytrityloxymethyl)benzylamine (5) (455 mg, 1.04 mmol) and 1,1′-carbonyldiimidazole (170 mg, 1.05 mmol) in THF (52 mL) was stirred for 24 hours at a room temperature under Ar atmosphere. TLC was used to confirm there was no starting material in the reaction mixture. Then, to the suspension was added dropwise a solution of 2-aminomethyl-6-[(tert-butyldimethylsilyloxy)methyl]pyridine (3) (593 mg, 2.35 mmol) in THF (13 mL), and further stirred for 48 hours. The reaction mixture was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (CHCl3:MeOH=100:1) to give N-[3-(4,4′-dimethoxytrityloxymethyl)benzyl]-N′-{[6-(tert-butyldimethylsilyloxy)methylpyridin-2-yl]methyl}urea (6) (406 mg, 54%) as a colorless oil.

Workup

  1. stirringfurther stirred for 48 hours
  2. customThe reaction mixture was evaporated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (CHCl3:MeOH=100:1)

Sources & evidence

ORD record
ord-42cc2525829e47edbf7bfad8fb26d70d
Source dataset
uspto-grants-2014_01
Patent number
US08633304B2

Reaction notes

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