HCID 86647542, compound → HCID 178465188, compound

Participants

Reaction Steps

A solution of 1-[2-chloro-6-[(2,2-diphenylethyl)amino]-9H-purin-9-yl]-1-deoxy-N-ethyl-β-D-ribofuranuronamide (18.0 g,0.0344 mole) in dimethylsulphoxide (100 ml) was heated at 120° under nitrogen with trans-cyclohexane-1,4-diamine (29.5 g, 0.258 mole) for 48h. The cooled mixture was diluted with ethyl acetate (1 l) and water (500 ml). The aqueous phase, which contained a considerable amount of oil, was separated from the ethyl acetate. The water was decanted from the oil and then extracted with ethyl acetate (100 ml) and the ethyl acetate solutions were combined, dried (MgSO4) and evaporated to leave a froth (9.2 g). The oil was dissolved in ethanol (500 ml) and the solution was evaporated to leave a solid which was dried in vacuo. The solid was leached with ethanol (3×200 ml) and the filtered solution was evaporated in vacuo to leave a froth (11.1 g). The two product fractions were combined and purified by column chromatography on flash silica eluted with dichloromethane:ethanol:0.88 ammonia (30:8:1) to give the title compound (17.11 g). The product had nmr(δ,CDCl3) including 1.1(t,3H), 1.1-1.35(m,4H),1.75-1.95(m,2H), 1.95-2.2(m,2H), 3.05-3.25(m,1H), 3.2-3.5(m,1H), 4.5-4.8(m,1H), 4.1-4.3(m,2H), 4.35(t,1H), 4.5(d,1H), 4.67(d,1H), 4.8(m,2H), 5.7-5.9(m,1H), 5.8(d,1H), 7.1-7.4(m,10H), 7.47(s,1H).

Provenance & Evidence