2,6-Lutidine → Benzoic acid 2-(2-acetylamino-6-oxo-1,6-dihydro-purin-9-yl)-5-(2-phosphono-vinyl)-tetrahydro-furan-3-yl ester

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Reaction Steps

A suspension of compound 9.9 (128 mg, 0.173 mmol) in MeCN (5 mL) was treated with 2,6-lutidine (0.08 mL, 0.7 mmol) and bromotrimethylsilane (0.3 mL, 2.27 mmol) and stirred at room temperature for 2 h. The mixture was evaporated and co-evaporated with MeCN. The residue was dissolved in MeOH—H2O (1:1, 10 mL) and treated with NaOH (1 N, 3 mL). The mixture was stirred at room temperature for 16 h then at 45° C. for 1 h, and concentrated under reduced pressure. The residue was subjected to reverse phase HPLC eluting with 0-25% CH3CN in water to give the desired product 9.10 (32 mg, 48%). 1H NMR (D2O) δ 2.1 (m, 2H), 4.55 (m, 1H), 4.8 (m, 1H), 5.7 (d, 1H, J=1.5), 5.9 (m, 1H), 6.1(m, 1H), 7.7 (s, 1H). 31P NMR (D2O) d 17.17. LRMS (ESI) MH+ C11H14N5O6P requires 344.2. Found 344.0.

Provenance & Evidence