Trimethyl orthoformate → HCID 58654417, compound

Participants

Reaction Steps

NaBH3CN (76 mg, 1.2 mmol) was added all at once to a stirred solution of 2-(2-(1H-imidazol-1-yl)-6-methylpyrimidin-4-yl)-N-methylpyrrolidine-3-carboxamide (230 mg, 0.80 mmol), tert-butyl benzo[d][1,3]dioxol-5-ylmethyl(2-oxoethyl)carbamate (280 mg, 0.95 mmol), acetic acid (100 μL, 1.59 μmol) and trimethyl orthoformate (20 ml). The reaction mixture stirred at rt for 16 h then water (20 mL) was added. The solution was extracted with EtOAc (2×20 mL), the combined organic layers were dried over Na2SO4, filtered and concentrated under vacuum. The residue was purified using column chromatography (20:1 CHCl3/MeOH) to afford 100 mg (22%) of tert-butyl 2-(2-(2-(1H-imidazol-1-yl)-6-methylpyrimidin-4-yl)-3-(methylcarbamoyl)pyrrolidin-1-yl)ethyl(benzo[d][1,3]dioxol-5-ylmethyl)carbamate as a colorless oil.

Provenance & Evidence