Toluene → HCID 178453340, compound

Participants

Reaction Conditions

Reaction Steps

Add copper(II)sulfate pentahydrate (0.022 g; 0.2 equiv; 0.088 mmoles) and L-ascorbic acid sodium salt (0.175 g; 2.0 equiv; 0.88 mmoles) to a deoxygenated solution of tert-butyl N-but-3-ynyl-N-[2-[2-(indan-2-ylamino)-5,7-dihydropyrrolo[3,4-d]pyrimidin-6-yl]-2-oxo-ethyl]carbamate (0.204 g; 1.0 equiv; 0.44 mmoles) in dimethylformamide (6 mL) and water (3 mL) (including toluene (0.05 mL) as an internal standard). Heat to 90° C. and then add azidotrimethylsilane (0.47 mL; 8 equiv; 3.54 mmoles) dropwise with continued stirring at 90° C. Stir for 3 hours, then dilute the reaction mixture with water (100 mL) and ethyl acetate (50 mL). Extract with ethyl acetate (3×50 mL), and wash the combined organic extracts with brine. Dry the organics over magnesium sulfate, filter, and concentrate. Purify the crude product by column chromatography (0 to 10% methanol in ethyl acetate) to give tert-butyl {2-[2-(2,3-dihydro-1H-inden-2-ylamino)-5,7-dihydro-6H-pyrrolo[3,4-d]pyrimidin-6-yl]-2-oxoethyl}[2-(1H-1,2,3-triazol-5-yl)ethyl]carbamate (0.157 g; 70%) as a yellowish foam: MS (m/z): 505(M+1).

Provenance & Evidence