Azidotrimethylsilane → HCID 178520884, compound

Participants

Reaction Steps

Add copper(II) sulfate pentahydrate (0.037 g; 0.2 equiv; 0.147 mmoles) and L-ascorbic acid sodium salt (0.291 g; 2.0 equiv; 1.47 mmoles) to a solution of 1-[2-(2,3-dihydro-1H-inden-2-ylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl]-3-(prop-2-yn-1-yloxy)propan-1-one (0.277 g; 1.0 equiv; 0.74 mmoles) in dimethylformamide (4 mL) and water (4 mL). Evacuate the system twice and backfill with nitrogen. Add azidotrimethylsilane (0.784 mL; 8.0 equiv; 5.89 mmoles) and heat the heterogeneous mixture to 90° C. for 1 hour. Dilute the reaction mixture with water (250 mL) and ethyl acetate (50 mL) and extract with ethyl acetate (3×50 mL). Wash the combined organic extracts with brine (30 mL), dry over sodium sulfate, filter, and concentrate in vacuo to a yellow/orange oil. Purify the crude product by column chromatography (ethyl acetate to 10% methanol in ethyl acetate) to afford the desired 1-[2-(2,3-dihydro-1H-inden-2-ylamino)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl]-3-(1H-1,2,3-triazol-4-ylmethoxy)propan-1-one (0.135 g; 44%): MS (m/z): 420 (M+1).

Provenance & Evidence