A mixture of 1-(1-methylpiperidin-4-yl)-7-trifluoromethanesulfonyloxynaphthalene (0.304 g, 0.819 mmol), 5-trimethylstannylpyrimidine (0.220 g, 0.905 mmol), triethylamine (0.55 mL, 3.95 mmol), lithium chloride (0.107 g, 2.53 mmol), bis(triphenylphosphine)palladium chloride (0.029 g, 0.041 mmol), and butylated hydroxytoluene (BHT, approx. 0.01 g, antioxidant) in dimethylformamide (15 mL) was heated to 115° C. for 1 hour. The reaction was cooled and diluted with ethyl acetate. The mixture was extracted with a mixture of 1N lithium chloride (25 mL) and 1N sodium hydroxide (3 mL), 1N lithium chloride and brine. The organic phase was dried over calcium sulfate and concentrated. The residue was flash chromatographed on silica gel (1×2.5 inches packed with 75% ethyl acetate/hexane). Elution proceeded as follows: 75% ethyl acetate/hexane, 225 mL, nil; ethyl acetate, 200 mL, nil; 1% methanol/ethyl acetate, 200 mL, nil; 5% methanol/ethyl acetate, 300 mL, nil; and 7% methanol/1% triethylamine/ethyl acetate, 250 mL, 0.130 g (52%) of 1-(1-methylpiperidin-4-yl)-7-pyrimid-5-yl-naphthalene as a tan foam. A sample triturated with ether afforded white crystals which had: Mp 121.5°-123° C.; 1H NMR (250 MHz, CDCl3) δ 9.27 (s, 1H), 9.08 (s, 2H), 8.26 (s, 1 H), 8.03 (d, J=8.5 Hz, 1H), 7.78 (dd, J=3, 6.5 Hz, 1H), 7.69 (dd, J=1.5, 8.5 Hz, 1H), 7.57-7.50 (m, 2H), 3.36 (sym m, 1H), 3.09 (br d, J=12 Hz, 2H), 2.40 (s, 3H), 2.28 (sym m, 2H), 2.06-1.90 (m, 4H). Analysis calculated for C20H21N3 : C, 79.17; H, 6.98;N, 13.85. Found: C, 78.46; H, 7.14; N, 13.89. HRMS m/e 303.1731. Observed m/e 303.1700.
