Sodium borohydride → HCID 58574398, compound

Participants

Reaction Steps

To a solution of 3-((3-fluorophenyl)ethynyl)-6H-pyrido[2,1-b]quinazoline-8,11(7H,9H)-dione (0.2 g, 0.6 mmol, 1 equiv) in THF (15 mL) was added NaBH4 (45.6 mg, 1.2 mmol, 2 equiv) in portions. After stirring at rt for 30 minute, the reaction mixture was quenched with water and extracted with ethyl acetate (3×50 mL). The combined organic layers were dried over Na2SO4. After filtration and concentration, the residue was purified by silica gel chromatography to give the desired product. MS (ESI): 335 (M+H+); 1H NMR (300 MHz, CDCl3) δ 8.24-8.21 (d, J=8.19 Hz, 1H), 7.76 (s, 1H), 7.56-7.53 (dd, J=8.22, 1.41 Hz, 1H), 7.37-7.34 (m, 2H), 7.27-7.26 (m, 1H), 7.13-7.06 (m, 1H), 4.53-4.51 (m, 1H), 4.34-4.28 (m, 1H), 4.05-3.99 (m, 1H), 3.52-3.22 (m, 1H), 3.03-2.93 (m, 1H), 2.23-2.16 (m, 1H), 2.11-2.02 (m, 2H). mGluR5 PAM EC50: +++. Fold shift at 10 μM: ++.

Provenance & Evidence