Reaktion #167966

Reaktionsgleichung

(R)-1-(3-methyl-4-(2-(3-methyl-1-tosyl-1H-indol-4-yl)-6-(2-methyl-5-(3-methyloxetan-3-yl)phenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)piperazin-1-yl)ethanone

ammonium hydroxide

KOH

→

(R)-1-(3-methyl-4-(2-(3-methyl-1H-indol-4-yl)-6-(2-methyl-5-(3-methyloxetan-3-yl)phenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)piperazin-1-yl)ethanone

Lösungsmittel

EtOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenThe mixture was concentrated
2. 2
   Sonstigepartially purified by FCC (0-6% MeOH in DCM)
3. 3
   SonstigeFurther purification with HPLC (C18, 15-85% CH3CN in H2O with 0.1% NH4OH)

Vorschrift

A mixture of (R)-1-(3-methyl-4-(2-(3-methyl-1-tosyl-1H-indol-4-yl)-6-(2-methyl-5-(3-methyloxetan-3-yl)phenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)piperazin-1-yl)ethanone (0.104 g, 0.145 mmol), 30% ammonium hydroxide (0.854 mL, 21.70 mmol) and KOH (0.073 g, 1.302 mmol) in EtOH (4 mL) was heated in a microwave reactor at 100° C. for 30 min. The mixture was concentrated and partially purified by FCC (0-6% MeOH in DCM). Further purification with HPLC (C18, 15-85% CH3CN in H2O with 0.1% NH4OH) provided (R)-1-(3-methyl-4-(2-(3-methyl-1H-indol-4-yl)-6-(2-methyl-5-(3-methyloxetan-3-yl)phenyl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)piperazin-1-yl)ethanone. 1H NMR (400 MHz, DMSO-d6 at 120° C.) δ ppm 10.50 (br. s., 1 H) 7.42 (d, J=8.08 Hz, 1 H) 7.25 (d, J=7.20 Hz, 1 H) 7.19 (d, J=7.83 Hz, 1 H) 7.07-7.15 (m, 2 H) 6.97 (s, 1 H) 6.90 (d, J=7.96 Hz, 1 H) 4.79 (d, J=5.43 Hz, 2 H) 4.53 (d, J=5.05 Hz, 2 H) 4.05-4.19 (m, 3 H) 3.91 (br. s., 1 H) 3.75 (br. s., 1 H) 3.56 (d, J=13.26 Hz, 1 H) 3.22-3.48 (m, 5 H) 3.00 (t, J=5.62 Hz, 2 H) 2.29 (s, 3 H) 2.07 (s, 3 H) 1.99-2.04 (m, 3 H) 1.65 (s, 3 H) 1.17 (d, J=6.44 Hz, 3 H); MS (ESI+) m/z 565.4 (M+H)+.

Quelle