Methylhydrazine → 9-[1-(t-Butyldimethylsilyloxy)-4-(diethoxyphosphorylmethoxy)but-2-oxy]adenine

Participants

Reaction Conditions

Reaction Steps

A solution of 9-[1-(t-butyldimethylsilyloxy)-4-(diethoxyphosphorylmethoxy)but-2-oxy]-6-phthalimidopurine (550 mg, 0.87 mmol) in dichloromethane (10 ml) was treated with methylhydrazine (0.05 ml, 0.96 mmol) and stirred for 30 min at 20° C. The reaction mixture was filtered, the solvent evaporated in vacuo and the residue chromatographed on silica, eluting with chloroform-methanol 40:1, affording 9-[1-(t-butyldimethylsilyloxy)-4-(diethoxyphosphorylmethoxy)-but-2-oxy]adenine (380mg, 87%) as a clear oil. νmax (film) 3340, 3200, 1730, 1650, 1600 and 1470 cm-1, δH (CDCl3) 0.04 (6H, s, CH3SiCH3), 0.87 (9H, s, (CH3)3CSi), 1.33 (6H, t, J7.1 Hz, 2×CH3CH2), 2.08 (2H, m, SiOCH2CHCH2), 3.80-3.90 (4H, m, CH2OSi+CH2P), 3.99 (2H, m, CH2OCH2P), 4.16 (4H, m, 2×CH3CH2), 4.61 (1H, m, CHON), 5.68 (2H, br.s, D2O exchangeable, NH2), 8.04 (1H, s, H- 2/H-8), 8.34 (1H, s, H-2/H-8); m/z (FAB+ve Ion), 526 (MNa+), 504 (MH+); Found: C, 47.35; H, 7.68; N, 13.67% C20H38N5O6PSi requires C, 47.50; H, 7.60; N, 13.91%.

Provenance & Evidence