Azidotrimethylsilane → HCID 178523291, compound

Participants

Reaction Steps

Add copper(II)sulfate pentahydrate (0.049 g; 0.2 equiv; 0.20 mmoles) and L-ascorbic acid sodium salt (0.388 g; 2.0 equiv; 1.96 mmoles) to a deoxygenated solution of 2-(2,3-dihydro-1H-inden-2-ylamino)-N-(pent-4-yn-1-yl)-5,7-dihydro-6H-pyrrolo[3,4-d]pyrimidine-6-carboxamide (0.354 g; 1.0 equiv; 0.98 mmoles) in dimethylformamide (3.26 mL) and water (3.26 mL). Add azidotrimethylsilane (1.04 mL; 8 equiv; 7.84 mmoles) and heat the mixture to 90° C. for 1 hour, the cool to ambient temperature and stir for 16 hours. Concentrate the solution to dryness, and purify the resulting orange semisolid by column chromatography (0 to 10% methanol in ethyl acetate) to afford 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-(1H-1,2,3-triazol-4-yl)propyl]-5,7-dihydro-6H-pyrrolo[3,4-d]pyrimidine-6-carboxamide (0.085 g; 21%) as a solid: MS (m/z): 405(M+1).

Provenance & Evidence