Sodium Bicarbonate → 3,3''-Dimethyl-1',2',3',4',5', 6'-hexahydro-cis-[2,2';6',2'']terpyridine

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Reaction Steps

To a solution of 1′-allyl-3,3″-dimethyl-1′,2′,3′,4′,5′,6′-hexahydro-cis-[2,2′;6′,2″]terpyridine (142 mg, 0.462 mmol) in CH2Cl2 was added 1,3-dimethylbarbaturic acid (361 mg, 2.31 mmol) and Pd(PPh3)4 (53 mg, 0.046 mmol) and the reaction mixture was stirred for 20 h. Saturated solution of NaHCO3 (10 mL) was added and the mixture was extracted with CH2Cl2 (3 times 20 mL). The organic extracts were dried (MgSO4), filtered and concentrated. The crude material was purified by flash column chromatography on silica gel (9:1:0.2 CH2Cl2-MeOH—NH4OH) to provide 105 mg (85%) of the 3,3″-dimethyl-1′,2′,3′,4′,5′, 6′-hexahydro-cis-[2,2′;6′,2″]terpyridine as a clear oil. 1H NMR(CDCl3) δ 1.51-1.63 (m, 2H), 1.76-1.85 (m, 3H), 2.11-2.15 (m, 1H), 2.37 (s, 6H), 3.10-3.30 (m, 1H), 4.22 (d, 2H, J=10.8 Hz), 7.02 (dd, 2H, J=7.5, 4.5 Hz), 7.38 (d, 2H, J=7.5 Hz), 8.45 (d, 2H, J=4.5 Hz); 13C NMR (CDCl3) δ 18.68, 25.84, 32.28, 57.60, 121.96, 129.73, 138.04, 147.31, 160.94; ES-MS m/z 269.1 (M+H). Anal. Calcd. for C17H21N3.0.1CH2Cl2: C, 74.45; H, 7.75; N, 15.23. Found: C, 74.70; H, 7.80; N, 15.18.

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