Toluene (50 mL) was added to a large Schlenk vessel charged with (+/-)-trans‑1,2‑diaminocyclohexane (1.0 g, 8.8 mmol), 2-bromo-6-methyl pyridine (3.0 g, 18 mmol), (±)-BINAP (218 mg, 0.35 mmol), [Pd₂(dba)₃] (160 mg, 0.18 mmol) and NaOBu^t (2.4 g, 25 mmol).  The resulting deep red/brown mixture was heated for 4 h at 80°C with stirring.  On cooling to room temperature diethyl ether (50 mL) was added.  The resultant yellow mixture was washed with brine (2 x 30 mL), dried over MgSO₄ and the solvent removed by evaporation under reduced pressure.  The yellow product was recrystallised from pentane / diethyl ether (yield 1.72 g, 60 %).

¹H NMR (293 K, d₆-benzene) d 1.25 (m, 4H, cyclohexane-CH₂), 1.58 (m, 2H, cyclohexane-CH₂), 2.30 (m, 2H, cyclohexane-CH₂), 2.52 (s, 6H, Py-CH₃), 4.05 (m, 2H, ipso cyclohexane‑CH), 5.39 (s, 2H, NH), 5.97 (d, ³J_HH = 7 Hz, 2H, Py-CH), 6.34 (d, ³J_HH = 7 Hz, 2H, Py-CH), 7.06 (t, ³J_HH = 7 Hz, 2H, Py-CH).

¹³C{¹H} NMR (293 K d₆-benzene) d 25.1 (Py-CH₃), 25.6 (cyclohexane-CH₂), 33.6 (cyclohexane-CH₂), 56.5 (cyclohexane-CH), 105.9 (Py-CH), 111.6 (Py-CH), 137.6 (Py-CH), 157.0 (PyCqCH₃), 159.3 (PyNCqN).

IR (nujol, cm^-1): 3292, 2726, 2669, 1605, 1582, 1519, 1336, 1295, 1226, 1153, 1115, 1099, 1029, 986, 948, 933, 778, 728. 

Anal. Calcd. for C₁₈H₂₄N₄: C, 72.94; H, 8.16; N, 18.90.  Found: C, 73.06; H, 8.09; N, 18.86.

MS (CI) m/z 297 (M⁺), 202 (M⁺-PyCH₃), 187 (M⁺-NH and PyCH₃), 109 (M⁺-2 x PyCH₃).

E. J. Crust, I. J. Munslow and P. Scott, Journal of Organometallic Chemistry, 2005, 690, 3373-3382.http://dx.doi.org/10.1016/j.jorganchem.2005.04.019