Reacción #654851

Ecuación de reacción

(4S,2R,3R,5R)-2-(6-amino-2-iodopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

compound 1

(4S,2R,3R,5R)-2-(6-amino-2-iodopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

prop-2-ynyloxybenzene

triethylamine

→

compound 10

Rendimiento 38.1%

(4S,2R,3R,5R)-2-{6-amino-2-[3-(2-phenylphenoxy)prop-1-ynyl]purin-9-yl}-5-(hydroxymethyl)oxolane-3,4-diol

Rendimiento 38.1%

Disolventes

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   Concentraciónthe reaction was concentrated in vacuo
2. 2
   Otrothe residue purified by preparatory thin layer chromatography (methylene chloride:methanol 9:1)

Procedimiento

To a solution of (4S,2R,3R,5R)-2-(6-amino-2-iodopurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol (compound 1) (50 mg, 0.126 mmol) and prop-2-ynyloxybenzene (22 δ, 0.1605 mmol) in N,N-dimethylformamide (1 ml) and triethylamine (21 δ, 16.065 mmol) at 23° C. was added copper iodide (5 mg, 0.026 mmol) and dichlorobis(triphenylphosphine)palladium(II) (22 mg, 0.031 mmol) catalyst. After being stirred in a sealed reacti-vial at 80 C for 6 hours, the reaction was concentrated in vacuo, the residue purified by preparatory thin layer chromatography (methylene chloride:methanol 9:1) to afford compound 10 (9.6 mg, 0.024 mmol) in 20% yield. 1H NMR(CDCl3:CD3OD 9:1) δ 3.02-3.04 (m, 1H), 3.07 (s, 1H), 3.55, 3.74 (dd, 2H), 4.02 (s, 1H), 4.11-4.13 (m, 1H), 4.48-4.52 (m, 1H), 4.72 (s, 2H), 5.65 (d, 1H), 6.75-6.82 (m, 3H), 7.08-7.12 (m, 2H), 7.94 (s, 1H).

Fuente