Potassium Hydroxide → (R)-1-(4-(6-(5-isopropyl-2-methylphenyl)-2-(3-methyl-1H-indol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)-3-methylpiperazin-1-yl)ethanone

Participants

Reaction Conditions

Reaction Steps

(R)-1-(4-(6-(5-Isopropyl-2-methylphenyl)-2-(3-methyl-1-tosyl-1H-indol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)-3-methylpiperazin-1-yl)ethanone was dissolved in EtOH (2 mL), then NH4OH (0.54 mL, 13.7 mmol) was added followed by KOH (46 mg, 0.821 mmol). The mixture was heated in a microwave reactor at 100° C. for 1 h. The reaction was then diluted with EtOAc and washed with brine. After concentration, the resulting residue was purified by HPLC (C18, 15-85% acetonitrile in H2O with 0.1% NH4OH) to provide (R)-1-(4-(6-(5-isopropyl-2-methylphenyl)-2-(3-methyl-1H-indol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)-3-methylpiperazin-1-yl)ethanone. 1H NMR (400 MHz, CD3CN) δ ppm 9.15 (br. s., 1 H) 7.46 (d, J=8.08 Hz, 1 H) 7.26 (d, J=7.33 Hz, 1 H) 7.16 (dd, J=16.29, 7.96 Hz, 2 H) 7.06 (d, J=13.64 Hz, 2 H) 6.91 (dd, J=7.58, 1.52 Hz, 1 H) 3.98-4.16 (m, 4 H) 3.46-3.67 (m, 2 H) 3.26-3.46 (m, 4 H) 2.84-3.13 (m, 4 H) 2.26 (s, 3 H) 2.00-2.06 (m, 6 H) 1.23 (d, J=6.82 Hz, 6H) 1.11-1.21 (m, 3 H); MS (ESI+) m/z 537.4 (M+H)+.

Provenance & Evidence