Ceric ammonium nitrate → N7-((2-Hydroxyethoxy)methyl)guanine

Participants

Reaction Conditions

Reaction Steps

To a solution of 8 (1.36 g, 4.10 mmol) in a mixture of CH3CN (30 mL) and water (10 mL) was added CAN (2.25 g, 4.10 mmol) at 0° C. The stirred reaction mixture was allowed to warm-up to 25° C. within 1.0 h. Water (30 mL) was added to afford a solid. Filtration and crystallization of the solid from EtOH/water (4:1) gave 9 (0.65 g, 2.88 mmol) in 70% yield: mp>280° C. (dec.); Rf(hexanes/EtOAc=1:2) 0.08; UV (EtOH) λmax 289 (ε 16,000); 1H NMR (DMSO-d6) δ 3.61-3.82 (m, 4H, O(CH2)2O), 4.85 (br s, 1H, OH), 5.81 (s, 2 H, H2C1′), 5.96 (br s, 2 H, NH2), 6.61 (s, 1 H, NH), 8.67 (s, 1 H, HC8); 13C NMR (DMSO-d6) δ 60.91 (CH2OH), 70.01 (OCH2) 75.25 (C1′), 107.16 (C5), 143.92 (C8), 153.20 (C4), 154.40 (C2), 159.30 (C6); MS m/z 225 (M+). Anal (C8H11N5O3) C, H, N; calcd (%): 42.66, 4.92, 31.10; found (%): 42.75, 4.84, 31.21.

Provenance & Evidence