Bromoacetonitrile → HCID 118598909, compound

Participants

Reaction Steps

6-((6-Amino-5-methoxypyrimidin-4-yl)amino)-8-methyl-2H-spiro[imidazo[1,5-a]pyridine-3,4′-piperidine]-1,5-dione hydrochloride (5, 0.18 g, 0.44 mmol) was dissolved in dimethylformamide (5 mL). To this mixture N,N-diisopropylethylamine (0.23 g, 1.76 mmol) was added followed by bromoacetonitrile (79 mg, 0.66 mmol). The reaction mixture was stirred at room temperature for 2 h. After completion the reaction mixture was diluted with saturated ammonium chloride solution (50 mL). Yellow precipitate was filtered and dried under reduced pressure. The compound was then purified by prep purification to afford 2-(6-((6-amino-5-methoxypyrimidin-4-yl)amino)-8-methyl-1,5-dioxo-1,5-dihydro-2H-spiro[imidazo[1,5-a]pyridine-3,4′-piperidin]-1′-yl)acetonitrile (Cpd. No. 243) as white solid. Yield: 40 mg, 22%; MS (ESI) m/z 411.20 [M+1]+; 1H NMR (400 MHz, DMSO-d6 with d1-TFA) δ 8.37 (s, 1H), 8.27 (s, 1H), 4.49 (s, 2H), 3.76 (s, 3H), 3.74-3.71 (m, 2H), 3.56-3.40 (m, 4H), 2.43 (s, 3H), 1.90-1.87 (m, 2H).

Provenance & Evidence