Sodium Hydroxide → 4-(1,3,5-Trimethyl-1H-pyrazol-4-ylmethyl)-3'-(4-cyanophenyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazine

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Reaction Steps

Suspend 4-(3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl-3′-yl)-benzonitrile (0.179 g, 0.675 mmol) in tetrahydrofuran (4 mL). Add 1,3,5-trimethyl-1H-pyrazole-4-carbaldehyde (0.098 g, 0.71 mmol) in tetrahydrofuran (490 μL), then sodium triacetoxyborohydride (0.15 g, 0.071 mmol) and stir under nitrogen at room temperature for 3 hr. Add saturated aqueous sodium hydrogen carbonate (10 mL) followed by 2 N sodium hydroxide (1 mL) to the mixture and extract with DCM (3×20 mL). Pass the combined DCM extracts through an IST Phase Separator Frit®, concentrate, and purify (silica gel chromatography, eluting with 0:100 to 12:88 methanol:DCM), to give the title compound (153.5 mg, 59%). MS (ES): m/z=388 [M+H]+.

Provenance & Evidence