Water → (1r,cis)-4-(6-Amino-9h-purin-9-yl)-2-cyclopentene-1-methanol o-monophosphate

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Reaction Conditions

Reaction Steps

(1R,cis)-4-(6-Amino-9H-purin-9-yl)-2-cyclopentene-1-methanol (Example 1, 200 mg, 0.865 mmol) was dissolved in 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (2 mL). Phosphoryl chloride (0.24 mL, 0.26 mmol) was added to the stirred, cooled (0° C.) solution. After 1 minute, 1.0 M sodium hydrogen carbonate (3.3 mL, 3.3 mmol) was added and stirring was continued at 0° C. for 30 minutes and then at 25° C. for 1 hour. The reaction solution was diluted to 125 mL with deionized water and applied to a 1.1×7.0 cm DEAE Sepahadex A25 (Aldrich) ion exchange chromatography column which had been washed with 1.0 M ammonium bicarbonate buffer and then equilibrated with deionized water. The title compund was eluted with a 0 to 0.5 M gradient (2 L) of ammonium bicarbonate. The appropriate fractions were combined and the volatiles removed by evaporation in vacuo. The residue was redissolved in deionized water (20 mL) and evaporated in vacuo three times. Lyophylization of the residue from water gave the ammonium salt of the title compound (270 mg, 90% as mono ammonium salt, monohydrate); 1H-NMR (D2O) δ 8.10 (S, 2H), 6.14–6.20 (m, 1H), 5.84–5.90 (m, 1H), 5.48–5.58 (m, 1H), 3.71–3.86 (m, 2H), 3.02–3.14 (br m, 1H), 2.66–2.80 (m, 1H), 1.56–1.66 (m, 1H); 31P-NMR (D2O) 0.62. Mass spectrum (ES−) m/e 310 (M−H).

Provenance & Evidence