Potassium Carbonate → 6-[2-(4-cyclobutylpiperazin-1-yl)-2-oxoethyl]-5,6,7,8-tetrahydro-1,6-naphthyridin-2(1H)-one

A mixture of 5,6,7,8-tetrahydro-1,6-naphthyridin-2(1H)-one (98 mg, 0.653 mmol), 1-(chloroacetyl)-4-cyclobutylpiperazine (142 mg, 0.653 mmol), K2CO3 (360 mg, 2.61 mmol) and KI (12 mg, 0.07 mmol) in CH3CN (15 mL) is stirred at rt overnight. The solvent is removed in vacuo and the residue is partitioned between water (10 mL) and EtOAc (20 mL). The layers are separated and the aqueous layer is extracted with EtOAc (2×10 mL) and the combined extracts are dried and evaporated. The resulting oil is purified by PTLC with DCM/MeOH/NH4OH (100:5:0.5) to give the title compound as a light yellow solid. MS (M+1): 331.2; 1H NMR (δ, CDCl3): 7.13 (d, 1H0, 6.38 (d, 1H), 3.60 (q, 4H), 3.44 (s, 2H), 3.35 (s, 2H), 2.79 (s, 2H), 2.63-2.75 (m, 1H), 2.26 (q, 4H), 1.63-2.06 (m, 6H).