Ammonium fluoride → 1-cyclopropyl-3-((3-(4-hydroxybutyl)imidazo[1,2-a]pyrazin-2-yl)methyl)-1H-imidazo[4,5-c]pyridin-2(3H)-one

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A mixture of (E)-3-((3-(4-(tert-butyldimethylsilyloxy)but-1-enyl)imidazo[1,2-a]pyrazin-2-yl)methyl)-1-cyclopropyl-1H-imidazo[4,5-c]pyridin-2(3H)-one 11-a (480 mg, 0.978 mmole) and Pd/C 10% (52 mg, 0.05 eq) in MeOH (20 mL) was hydrogenated for 2 h. The reaction mixture was then filtered over dicalite and concentrated to dryness. The resulting white solid (480 mg, 84%) was used directly in the next step. It was redissolved in MeOH and ammonium fluoride (39 mg, 1.1 eq) was added. The reaction mixture was then heated at 60° C. overnight. After concentration, the crude was purified by Prep HPLC on (RP Vydac Denali C18-10 μm, 250 g, 5 cm), with the following mobile phase (0.25% NH4HCO3 solution in water, CH3CN), to give the targeted product P17 in 87% yield (320 mg). m/z=491 (M+H)+; 1H NMR (400 MHz, DMSO-d6) δ ppm 0.82-0.94 (m, 2H), 0.99-1.10 (m, 2H), 1.36-1.46 (m, 2H), 1.46-1.59 (m, 2H), 2.96 (tdd, J=6.96, 6.96, 3.64, 3.51 Hz, 1H), 3.08 (t, J=7.53 Hz, 2 H), 3.34-3.43 (m, 2H), 4.38 (t, J=5.14 Hz, 1H), 5.22 (s, 2H), 7.23 (dd, J=5.27, 0.75 Hz, 1H), 7.88 (d, J=4.52 Hz, 1H), 8.22 (d, J=5.27 Hz, 1H), 8.40 (s, 1H), 8.44 (dd, J=4.64, 1.38 Hz, 1H), 8.97 (d, J=1.51 Hz, 1H).

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