Potassium Carbonate → HCID 68594129, compound

Participants

Reaction Conditions

Reaction Steps

Stir 3′-chloro-4-(1,5-dimethyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl (153 mg, 0.50 mmol), potassium carbonate (166 mg, 1.20 mmol), 5-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-oxazole (163 mg, 0.60 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.006 g, 0.005 mmol) in N,N-dimethylacetamide (2 mL). Add water (1 mL), degas for 5 min., and then heat at 120° C. for 17 hr. Cool to room temperature, add water (5 mL) and extract with DCM (3×5 mL). Pass the combined DCM extracts through an IST Phase Separator Frit®. Concentrate the filtrate and purify by SCX-2® chromatography washing with methanol then eluting with 2.5 M ammonia in methanol. Recrystallize from DMSO:methanol (50:50, 2.4 mL), filter and wash with diethyl ether. Collect precipitate from filtrate, then combine solids to give the free base 4-(1,5-dimethyl-1H-pyrazol-4-ylmethyl)-3′-(4-oxazol-5-yl-phenyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl as a yellow solid (147 mg, 71%). Dissolve the free base (82 mg, 0.20 mmol) in acetonitrile, add 2 M aq. HCl then water. Lyophilize to give the title compound as yellow powder (65 mg, 72%). MS (ES): m/z=416 [M+H].

Provenance & Evidence