4-Aminopyridine → HCID 86726557, compound

Participants

Reaction Steps

Add 1,1′-carbonyldiimidazole (0.936 g; 5.66 mmoles) slowly dropwise to a −78° C. solution of 4-pentyn-1-ol (0.50 mL; 5.39 mmoles) in dichloromethane (18 mL). Allow the reaction to warm to ambient temperature for 30 minutes, then add half of this solution to a solution of N-indan-2-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine (0.581 g; 1.05 equiv; 2.18 mmoles), 4-pyridinamine, N,N-dimethyl-(0.258 g; 1.0 equiv; 2.08 mmoles), and triethylamine (0.58 mL; 2.0 equiv; 4.15 mmoles). Warm the resulting pale yellow solution to ambient temperature and stir for 16 hours, then warm to 40° C. for an additional 24 hours. Cool the reaction mixture to ambient temperature and load directly onto a silica gel column. Purify by column chromatography (20 to 100% ethyl acetate in dichloromethane) to afford pent-4-yn-1-yl 2-(2,3-dihydro-1H-inden-2-ylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate (0.76 g; 88%): MS (m/z): 377(M+1).

Provenance & Evidence