Formaldehyde → HCID 53391360, compound

Participants

Reaction Conditions

Reaction Steps

A 25 mL round bottom flask was charged with ethyl 8-(piperazin-1-yl)-5-(thiophen-2-yl)imidazo[1,2-a]pyrazine-2-carboxylate (200 mg, 0.56 mmol), MeOH (15 mL), CH2Cl2 (15 mL), 40% aqueous formaldehyde (1 mL) and NaBH3(CN) (250 mg, 3.9 mmol). The mixture was stirred at 25° C. for 1 h. Reaction progress was monitored by LC-MS. Work-up: the solvent was evaporated. The residue was purified by flash column chromatography on silica gel with a 1:20 MeOH/CH2Cl2, to afford 150 mg (72%) of the product. 1H NMR (300 MHz, CDCl3) δ: 8.33 (s, 1H), 7.50 (s, 1H), 7.48 (dd, J=5.4, 1.2 Hz, 1H), 7.35 (dd, J=3.3, 1.2 Hz, 1H), 7.20 (dd, J=5.4, 3.3 Hz, 1H), 4.43-4.38 (m, 6H), 2.59 (t, J=5.1 Hz, 4H), 1.40 (t, J=6.9 Hz, 3H). MS m/z: 372 (M+H+).

Provenance & Evidence