Ethyl Acetate → 2-chloro-3-(tetrahydro-2H-pyran-4-yl)pyrazine

Participants

Reaction Conditions

Reaction Steps

A mixture of copper(I) iodide (0.066 g, 0.35 mmol), Pd(dppf)Cl2 (0.14 g, 0.18 mmol), and 2,3-dichloropyrazine (0.52 g, 3.50 mmol) in DMA (3 mL) was placed under argon atmosphere using 3 evacuation/backfill cycles. A solution of (tetrahydro-2H-pyran-4-yl)zinc(II) iodide (about 3.50 mmol, prepared in example 6, step 1) was added dropwise via syringe and the mixture was heated to 80° C. for 4 h, then cooled to RT. Ethyl acetate and saturated aqueous ammonium chloride were added, the resulting layers were separated, and the organic layer was washed with water (2×), brine, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to give an oil. The oil was purified by silica gel chromatography to give 2-chloro-3-(tetrahydro-2H-pyran-4-yl)pyrazine (0.20 g, 1.03 mmol, 29% yield) as a light yellow solid.

Provenance & Evidence