Lithium Hexamethyldisilazide → 1-(6-Methoxypyridin-2-yl)-2,2-dipyridin-3-ylethanamine

Participants

Reaction Conditions

Reaction Steps

LiHMDS (2.45 mL, 1.2 M in THF, 2.94 mmole) was added to a flame-dried round bottom flask. The mixture was cooled to 0° C. then 6-methoxypyridine-2-carbaldehyde (Comins, Daniel L.; Killpack, Michael O. J. Org. Chem. 1990, 55, 69-73, 161 mg, 1.18 mmole) was added. After 30 minutes di-3-pyridylmethane (200 mg, 1.18 mmole) in dry THF (2.0 mL) was added. After 2 hr the mixture was warmed to RT, quenched with saturated NH4Cl, and extracted with CH2Cl2(3×) and iBuOH (2×). The combined organic layers were dried (MgSO4), filtered, and concentrated. The residue was taken up in MeOH (5 mL) and H2NOH (0.4 mL, 50% in H2O) was added. After 18 hr the mixture was concentrated. Flash column (gradient, 0-10% MeOH/CH2Cl2) gave 1-(6-methoxypyridin-2-yl)-2,2-dipyridin-3-ylethanamine as a pale yellow oil (168 mg, 47%): 1H-NMR (500 MHz, CDCl3) δ 8.64 (d, J=1.95 Hz, 1H), 8.51 (dd, J=1.46 and 3.17 Hz, 1H), 8.36 (d, J=1.95 Hz, 1H), 8.32 (dd, J=1.46 and 3.18 Hz, 1H), 7.76 (d, J=7.82 Hz, 1H), 7.49 (d, J=8.06 Hz, 1H), 7.37-7.27 (m, 2H), 7.09 (m, 1H), 6.56 (d, J=7.08 Hz, 1H), 6.52 (d, J=7.81 Hz, 1H), 4.59 (d, J=9.28 Hz, 1H), 4.42 (d, J=9.28 Hz, 1H), 3.91 (s, 3H).

Provenance & Evidence