3-Oxetanone → (R)-6-(5-isopropyl-2-methylphenyl)-2-(3-methyl-1-tosyl-1H-indol-4-yl)-4-(3-methyl-4-(oxetan-3-yl)piperazin-1-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

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A mixture of (R)-6-(5-isopropyl-2-methylphenyl)-2-(3-methyl-1-tosyl-1H-indol-4-yl)-4-(3-methylpiperazin-1-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (53 mg, 0.082 mmol), oxetan-3-one (17.6 mg, 0.245 mmol) and Na(AcO)3BH (51.9 mg, 0.245 mmol) in DCM (3 mL) was stirred at rt for 3 h. At that point starting material remained so additional oxetan-3-one (17.7 mg, 0.245 mmol) and Na(AcO)3BH (51.9 mg, 0.245 mmol) were added and the reaction stirred for 16 h. The mixture was then diluted with EtOAc, washed with sat NaHCO3 and brine. The organic layer was then dried over Na2SO4, filtered and concentrated. The residue was purified by FCC (5-65% EtOAc/heptane) to provide (R)-6-(5-isopropyl-2-methylphenyl)-2-(3-methyl-1-tosyl-1H-indol-4-yl)-4-(3-methyl-4-(oxetan-3-yl)piperazin-1-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine. MS (ESI+) m/z 705.5 (M+H)+.

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