Methanol → Ammonium Hydroxide

Participants

Reaction Steps

A solution of 2-iodoadenosine (1 g, 2.5 mmol) and ammonium sulfate (0.033 g, 0.25 mmol) in hexamethyldisilazane (20 mL) was heated overnight at 80° C. The reaction was cooled to room temperature, concentrated in vacuo, and azeotroped with toluene. The residue was taken up in THF (10 mL) and Pd(PPh3)4 (0.144 g, 0.125 mmol) was added. The reaction mixture was heated at 68° C. for 10 minutes before the addition of trimethylaluminum (2.0M in hexanes, 5.0 mL, 5.0 mmol). Heating was continued for 3.5 h. After cooling to room temperature, MeOH was added to destroy excess trimethylaluminum. The reaction mixture was partitioned between CHCl3 and H2O. The aqueous layer was extracted with CHCl3 (2×50 mL). The combined organic layers were washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was taken up in MeOH:H2O (4:1) (25 mL) and ammonium chloride was added (400 mg). The reaction was heated at 65° C. for 3 h. When judged complete by TLC, the reaction was concentrated in vacuo and was subjected to silica gel column chromatography running 2% MeOH:DCM with 0.1% NH4OH to afford 2-methyl adenosine.

Provenance & Evidence