Potassium Carbonate → N-{[4-(4-{3-[cyclobutyl(methyl)amino]propoxy}phenyl)tetrahydro-2H-pyran-4-yl]methyl}pyridin-2-amine

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4-{4-[(pyridin-2-ylamino)methyl]tetrahydro-2H-pyran-4-yl}phenol (386 mg, 1.36 mmol), N-(3-chloropropyl)-N-methylcyclobutanamine (241 mg, 1.496 mmol) and potassium carbonate (280 mg, 2.03 mmol) were stirred in DMF (2 ml) at 45° C. for 24 hours until complete. Reaction was partitioned between ethyl acetate (40 ml) and saturated sodium bicarbonate solution (50 ml), then the organic layer washed with water (50 ml). Organic layer separated and dried over sodium sulphate, filtered and concentrated in vacuo. Crude product purified by flash chromatography on silica gel eluting with dichloromethane:methanol:ammonia (100:0:0 to 90:10:1 by volume) to give the title compound (165 mg, 30%). 1H NMR (400 MHz, CDCl3) δ 1.55-1.72 (m, 2H), 1.80-1.99 (m, 6H), 2.00-2.09 (m, 2H), 2.10-2.20 (m, 4H), 2.40 (t, 2H), 2.80 (quintet, 1H), 3.50 (d, 2H), 3.54-3.62 (m, 2H), 3.78-3.88 (m, 2H), 4.00 (m, 3H), 6.20 (d, 1H), 6.50 (t, 1H), 6.92 (d, 2H), 7.22 (d, 2H), 7.32 (t, 1H), 8.00 (d, 1H). LRMS APCI+ m/z 410 [MH]+. HRMS ESI+ m/z 410.2794[MH]+.

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