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

Participants

Reaction Steps

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.

Provenance & Evidence