Azidotrimethylsilane → HCID 178525384, compound

Participants

Reaction Steps

Add copper(II)sulfate pentahydrate (0.090 g; 0.2 equiv; 0.36 mmoles) and L-ascorbic acid sodium salt (0.714 g; 2.0 equiv; 3.61 mmoles) to a deoxygenated solution of pent-4-yn-1-yl 2-(2,3-dihydro-1H-inden-2-ylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate (0.754 g; 1.0 equiv; 1.80 mmoles) in dimethylformamide (15 mL) and water (15 mL). Add azidotrimethylsilane (1.92 mL; 8 equiv; 14.42 mmoles) and heat the reaction to 90° C. for 3 hours. Dilute the reaction mixture with water (250 mL) and ethyl acetate. Extract the mixture with ethyl acetate (3×50 mL). Wash the combined organic extracts with water (3×) and brine, dry over sodium sulfate, filter, and concentrate to a tan/orange oil. Purify the crude product by column chromatography (0 to 5% methanol in dichloromethane) to afford 3-(1H-1,2,3-triazol-4-yl)propyl 2-(2,3-dihydro-1H-inden-2-ylamino)-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate (0.26 g; 35%): MS (m/z): 420(M+1).

Provenance & Evidence