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

HRID 473229Notes

Reaction equation

HRID 473229 reaction equation
[CH3:1][O:2][C:3]1[CH:35]=[CH:34][C:6]([C:7]([O:22][CH2:23][C:24]2[CH:25]=[C:26]([CH:31]=[CH:32][CH:33]=2)[CH2:27][N:28]=[C:29]=[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.[NH2:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[C:40]([CH2:44][O:45][Si:46]([C:49]([CH3:52])([CH3:51])[CH3:50])([CH3:48])[CH3:47])[N:39]=1>>[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:31]=[CH:32][CH:33]=2)[CH2:27][NH:28][C:29]([NH:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[C:40]([CH2:44][O:45][Si:46]([C:49]([CH3:52])([CH3:51])[CH3:50])([CH3:47])[CH3:48])[N:39]=2)=[S:30])([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:35][CH:34]=2)=[CH:13][CH:12]=1

Participants

3

Reactant 2

HCID 668467232-Aminomethyl-6-[(tert-butyldimethylsilyloxy)methyl]pyridineHCID 866715143-(4,4'-Dimethoxytrityloxymethyl)benzyl isothiocyanate

Product 1

HCID 87326894N-[3-(4,4'-dimethoxytrityloxymethyl)benzyl]-N'-{[6-(tert-butyldimethylsilyloxymethyl)pyridin-2-yl]methyl}thioureaYield 110.4%

Procedure

To a solution of 3-(4,4′-dimethoxytrityloxymethyl)benzyl isothiocyanate (21) (332 mg, 0.69 mmol) in CDCl3 (4.6 mL) was added a solution of 2-aminomethyl-6-[(tert-butyldimethylsilyloxy)methyl]pyridine (3) (63.10 mg, 0.39 mmol) in CDCl3 (3 mL). The air was evacuated from the reaction system, and then Ar was charged therein. The reaction mixture was refluxed 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 purified by silica gel column chromatography (Hex:EtOAc=3:1 to 2:1) to give N-[3-(4,4′-dimethoxytrityloxymethyl)benzyl]-N′-{[6-(tert-butyldimethylsilyloxymethyl)pyridin-2-yl]methyl}thiourea (22) (316 mg, 62%) as a yellow oil.

Workup

  1. customThe air was evacuated from the reaction system
  2. additionAr was charged
  3. temperatureThe reaction mixture was refluxed for 5 hours
  4. customThen, the reaction mixture was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (Hex:EtOAc=3:1 to 2:1)

Sources & evidence

ORD record
ord-5e1a6c964a7547f190937c111cba9976
Source dataset
uspto-grants-2014_01
Patent number
US08633304B2

Reaction notes

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