Ammonia → 4-(2-Amino-1-hexen-1-yl)-1-beta-D-ribofuranosyl-pyrimidin-2-one

Participants

Reaction Steps

A solution of 14a (1.2 g, 1.9 mmol) in methanolic ammonia (saturated at −20° C.) was stirred in a pressure bottle for 18 hr. Evaporation of the solvents and flash chromatography of the residue using ethyl acetate/methanol (4:1) gave 17a as a light yellow solid, 0.47 g (77%). 1H-NMR (DMSO-d6): δ10.2 and 7.7 (2 bs, 2H, NH2); 7.83 (d, 1H, H-6, J6,5=6.9 Hz); 5.78 (s, 1H, H-1′); 4.72 (s, 1H, vinylic); 2.17, 1.50, 1.30 and 0.90 (4 m, 9H, n-butyl).

Provenance & Evidence