Cesium fluoride → HCID 60148745, compound

Participants

Reaction Conditions

Reaction Steps

To a round bottom flask were added 3-[2,4-di-morpholin-4-yl-7-(2-trimethylsilanyl-ethoxymethyl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-phenol (8.1 mg, 0.016 mmol) and cesium fluoride (72.4 mg, 0.477 mmol, 30 equiv) followed by acetone (6 mL). The reaction was heated for 6 hours at 40° C. The reaction was then quenched by adding aqueous saturated ammonium chloride solution (10 mL). Acetone was removed under reduced pressure and the aqueous phase was extracted with DCM (3×15 mL). The combined organic phase was removed under reduced pressure and the crude product was directly purified using reverse phase preparative HPLC (5% to 70% H2O/MeCN, with n-propanol in water as modifier) to obtain the desired product as a white solid (4.1 mg, 67.8% yield). LC/MS analysis method 7, mass (ES+) m/z 382.4, retention time 1.05 min 1HNMR (CDCl3): δ 10.15 (1H, brs), 7.15 (1H, t), 7.02 (1H, d), 6.67 (1H, brs), 6.65 (2H, m), 6.52 (1H, s), 3.82 ppm (8H, dt), 3.64 (8H, m)

Provenance & Evidence