Formaldehyde → HCID 53390142, compound

Participants

Reaction Steps

A 100 mL round bottom flask was charged with 5-(piperazin-1-yl)-8-(thiophen-2-yl)tetrazolo[1,5-c]pyrimidine hydrochloride (0.16 g, 0.49 mmol), CH2Cl2 (20 mL), methanol (10 mL), 40% aqueous formaldehyde (2 mL) and NaBH3(CN) (0.1 g, 1.7 mmol). The resulting solution was stirred at room temperature for 0.5 h. Work-up: the reaction mixture was diluted with saturated aqueous NaHCO3 and extracted with CH2Cl2 (50 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel with 1-10% MeOH in CH2Cl2 to afford 24 mg (16%) of the product as a white solid. 1H NMR (300 MHz, CD3OD) δ: 8.55 (s, 1H), 7.42 (dd, J=5.1, 1.2 Hz, 1H), 7.39 (dd, J=3.6, 1.2 Hz, 1H), 7.08 (dd, J=5.1, 3.6 Hz, 1H), 3.70-3.40 (br, 4H), 3.30-3.10 (br, 4H), 2.96 (s, 3H). MS m/z: 302 (M+H+).

Provenance & Evidence