Dimethylformamide → HCID 66744048, compound

Participants

Reaction Steps

A mixture of 6′-(pyridin-4-yl)-1′H-spiro[piperidine-4,2′-thieno[3,2-d]pyrimidin]-4′(3′H)-one in DMF (0.16 M, 0.50 mL, 0.080 mmol), acetaldehyde in DMF (0.20 M, 1 mL, 0.20 mmol) and sodium triacetoxyborohydride (40 mg, 0.19 mmol) was stirred for 16 h at room temperature. The reaction mixture was extracted with EtOAc (3.5 mL) and 2% aqueous sodium hydrogen carbonate (1 mL). After evaporating the organic solvent, the crude product was chromatographed on preparative HPLC (YMC CombiPrep. Hydrosphere C18, 10 mM NH4HCO3 in water/MeCN) to afford the title compound (2.4 mg, 9.1%):

Provenance & Evidence