Pyridine → 97845-82-4

Participants

Reaction Steps

To a solution of N2 -monomethoxytrityl-9-(4-monomethoxytrityloxy-3-hydroxymethylbut-1-yl)guanine (0.72 g, 0.9 mmol) in pyridine (4 ml) was added hexanoyl chloride (0.38 ml, 2.7 mmol) and the solution was stirred for 20 minutes. The mixture was precipitated in water (40 ml) and the resulting precipitate was stirred in 80% acetic acid (10 ml) at 80° for 45 minutes. The solvent was removed and the residue purified by column chromatography on silica gel eluting with chloroform-methanol mixtures (7:1, 5:1) to afford 9-(4-hexanoyloxy-3-hydroxymethylbut-1-yl)guanine (0.12 g, 38%), m p. 179°-181° C.; νmax 2960, 2930, 1730, 1690, 1630, and 1600 cm-1 : δH [(CD3)2SO] 0.84 (3 H, t, J 6.9 Hz, CH3), 1.24 (4 H, m, CH3 (CH2)2), 1.50 (2 H, quintet, J 7.3 Hz, CH2CH2CO), 1.6-1.8 (3 H, m, 2'-H and 3'-H), 2.26 (2 H, t, J 7.3 Hz, CH2CO), 3.40 (2 H, t, J 5 Hz, D2O exchange leaves d, CH2OH), 3.9-4.1 (4 H, m, 1'-H and CH2OCO), 4.60 (1 H, t, J 5.1 Hz, D2O exchangeable, 2-NH2), 7.67 (1 H, s, 8-H), and 10.49 (1 H, s, D2O exchangeable, 1-H); (Found: C, 52.63; H, 6.91; N, 18.75%; C16H25N5O4 requires: C, 54.69; H, 7.17; N, 19.93%).

Provenance & Evidence