1,1'-Carbonyldiimidazole → N,N'-bis{[6-(tert-butyldimethylsilyloxy)methylpyridin-2-yl]methyl}urea
Reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])[N:4]=1.[C:18]([N:25]1[CH:29]=[CH:28][N:27]=[CH:26]1)(N1C=CN=C1)=[O:19]>C1COCC1>[Si:11]([O:10][CH2:9][C:5]1[N:4]=[C:3]([CH2:2][NH:1][C:18]([NH:25][CH2:29][C:28]2[CH:2]=[CH:3][CH:8]=[C:26]([CH2:9][O:10][Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])[N:27]=2)=[O:19])[CH:8]=[CH:7][CH:6]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:12])[CH3:13]Participants
4
Procedure
2-Aminomethyl-6-[(tert-butyldimethylsilyloxy)methyl]pyridine (26) (380 mg, 1.50 mmol) and 1,1′-carbonyldiimidazole (150 mg, 0.92 mmol) were suspended in THF (10 mL). The air was evacuated from the reaction system, and then Ar was charged therein. The suspension was stirred for 24 hours at a room temperature. 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=50:1) to give N,N′-bis{[6-(tert-butyldimethylsilyloxy)methylpyridin-2-yl]methyl}urea (27) (384 mg, 96%) as yellow crystals.