CC(N)c1ccccc1.Clc1cnccn1>CC(=O)O.CC(=O)O.CC(C)(C)[O-].Cc1ccccc1.[Na+].[Pd].c1ccc(P(c2ccccc2)c2ccc3ccccc3c2-c2c(P(c3ccccc3)c3ccccc3)ccc3ccccc23)cc1>CC(Nc1cnccn1)c1ccccc1To a solution of 1-phenylethanamine (212 mg, 1.75 mmol) and 2-chloropyrazine (200 mg, 1.75 mmol) in toluene (10 mL) while bubbling N2 was added binap (141 mg, 0.23 mmol), sodium tert-butoxide (235 mg, 2.44 mmol) and palladium(II) acetate (51.0 mg, 0.23 mmol). The reaction mixure was heated at 70 oC for 3 hours. The reaction was concentrated, partitioned between ethyl acetate and water. The aqueous phase was extracted 3 times with ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated. The crude material was loaded on a 40g silica gel column and purified on a Teledyne Isco instrument, eluting with 20% to 70% ethyl acetate in heptane to provide N-(1-phenylethyl)pyrazin-2-amine (148 mg, 42.5 %) as a solid.
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