Methylhydrazine → HCID 19993538, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 9-[2-(t-butyldimethylsilyloxy)-3-(diethoxyphosphorylmethoxy)propoxy]-6-phthalimidopurine (0.99 g, 1.6 mmol) in dichloromethane (10 ml) was cooled to 0° C., treated with methylhydrazine (0.lml, 1.76 mmol) and stirred at 20° C. for 1.5 h. The reaction mixture was filtered and evaporated in vacuo and the residue dissolved in ether. The ether was filtered, evaporated in vacuo and the residue chromatographed twice on silica, eluting firstly with chloroform-methanol 20:1 and then with chloroform, to give 9-[2-(t -butyldimethylsilyloxy)-3-(diethoxyphosphorylmethoxy)propoxy]adenine (480mg, 61%) as a clear oil. νmax (film) 3350, 1650, 1600 and 1590 cm-1 ; δH (CDCl3) 0.07 (6H, S, CH3SiCH3), 0.88 (9H, S, (CH3)3CSi), 1.34 (6H, t, J6.8 Hz, 2×CH3CH2), 3.75 (2H, d, J5.2 Hz, CH2OCH2P), 3.87 (2H, d, J8.2 Hz, CH2P), 4.17 (4H, m, 2×CH3CH2), 4.22 (1H, m, CHOSi), 4.42 (1H, m, CH2ON), 4.53 (1H, m, CH2ON), 5.71 (2H, br.s, D2O exchangeable, NH2), 7.99 (1H, s, H-2/H-8), 8.36 (1H, s, H-2/H-8). Found: C, 45.57; H, 7.40; N, I3.65%; [M-H]+ 488.0297. C19H36N5O6PSi.0.7H2O requires C, 45.44; H, 7.50; N, 13.94%; [M-H]+ 488.0294.

Provenance & Evidence