2,6-Lutidine → ((2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxy-2-methyl-tetrahydrofuran-2-yloxy)methylphosphonic acid

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Reaction Steps

To a solution of compound 31.4 (20 mg, 0.048 mmol) in acetonitrile (2 mL) was added 2,6-lutidine (0.034 mL, 0.29 mmol) and then trimethylsilyl iodide (0.068 mL, 0.48 mmol). The mixture was stirred at room temperature for 1 h. After the reaction was done, 0.08 mL of 2,6-lutidine was added to the mixture and the mixture was concentrated under reduced pressure. The residue was then put into solution with water (2 mL) and treated with sodium hydroxide 1N to pH=10. The solution was then acidify to pH=3 using acetic acid and subjected to a reverse phase (YMC-Pack ODS-A) to give compound 31.5 (69 mg, 72% yield). 1H NMR (300 MHz, D2O): δ 1.42 (s, 3H), 3.33 (t, 1H, J=10.7), 3.51 (t, 1H, J=11.9), 4.12 (d, 1H, J=4.6), 5.18 (m, 1H), 6.10 (d, 1H, J=7.1), 8.24 (s, 1H), 8.55 (s, 1H). LRMS (ESI) MH+ C11H16N5O7P requires 362.3. Found 361.9.

Provenance & Evidence