Methylhydrazine → 6-(3-isopropyl-1-methyl-1H-pyrazol-5-yl)-4-methoxy-2-(3-methyl-1-tosyl-1H-indol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(4-methoxy-2-(3-methyl-1-tosyl-1H-indol-4-yl)-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-4-methylpentane-1,3-dione (350 mg, 0.624 mmol) in THF (3.3 mL), in a 2-5 mL microwave vial, was added Lawesson's reagent (278 mg, 0.687 mmol) and methyl hydrazine (0.049 mL, 0.94 mmol). The vessel was immediately sealed and heated via microwave irradiation at 120° C. for 10 minutes. The reaction was then cooled to room temperature and diluted with dichloromethane and water. The layers were separated and the aqueous layer was extracted two additional times with dichloromethane. The organic layers were combined, dried over Na2SO4, filtered, and concentrated. The resulting residue was purified via silica gel flash chromatography (45-67% ethyl acetate/heptanes) to provide 6-(3-isopropyl-1-methyl-1H-pyrazol-5-yl)-4-methoxy-2-(3-methyl-1-tosyl-1H-indol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine. MS (ESI+) m/z 571.4 (M+H)+.

Provenance & Evidence