Ethylenediamine → 2,6-Diaminopurine

Participants

Reaction Steps

To 2′-deoxyguanosine (2 mmol), dried by coevaporation with pyridine, suspended in 40 mL of pyridine and cooled in an ice bath under an argon atmosphere, trifluoroacetic anhydride (16 mmol) is added following the procedure of Kung and Jones (Tetraheron Lett., 32, 3919, 1991). After 40 minutes, ethylenediamine (30 mmol) is added and stirred for 24 h at room temperature. The reaction mixture is concentrated and purified by silica column chromatography. The product is guanylated with reagent 5 as in Example 8 and protected at N2-position with an isobutyryl group by treating with isobutyric anhydride, 5′-dimethoxytritylated at the 5′-position and purified. The resulting compound is treated with benzoic anhydride (N6 protection) and then phosphitylated following the procedures described above to afford the 2,6-diaminopurine derivative functionalized at the 6-position (35).

Provenance & Evidence