HCID 13869780, compound → 6-Amino Didesacetyl Famciclovir

Participants

Reaction Steps

A solution of 2,6-diamino-9-[2-(2,2-dimethyl-1,3-dioxan-5-yl)ethyl]purine (180 mg, 0.6 mmol) in 70% acetic acid (10 ml) was stirred for 1 hour at room temperature. The solvent was removed, the residue was suspended in methanol and sodium methoxide was added to neutralise. Column chromatography on silica gel eluting with chloroform-methanol mixtures (6:1, 4:1 and 3:1) gave 2,6-diamino-9-(4-hydroxy-3-hydroxymethylbut-1-yl)purine (95 mg, 63%), m.p. 187-190° C.; λmax (H2O, pH6.5) 215 (ε 25,500), 255 (ε 7,290), and 280 (ε 9,170) nm; νmax 3150, 1680, 1650, 1605, 1590, and 1410 cm−1; δH [(CD3)2SO] 1.46 (1H, m, CHCH2CH2), 1.73 (2H, q, J 7.1 Hz, CHCH2CH2), 3.3-3.5 (4H, ddd (ABX), JAB 10.6 Hz, JAX 5.5 Hz and JBX 5.9 Hz, 2×CH2O), 4.01 (2H, t, J 7.3 Hz, CH2N), 4.41 (2H, br, D2O exchangeable, 2×OH), 5.70 (2H, s, D2O exchangeable, NH2), 6.56 (2H, s, D2O exchangeable, NH2), and 7.69 (1H, s, 8-H) (Found: C, 46.09; H, 6.32; N, 31.69%; C10H16N6O2.0.1CHCl3 requires C, 45.91; H, 6.14; N, 31.81%).

Provenance & Evidence