Reaktion #160878

Reaktionsgleichung

Dess-Martin periodinane

N-{4-[4-amino-6-(1-hydroxyethyl)-7-(morpholin-4-ylmethyl)pyrrolo[2,1-f][1,2,4]-triazin-5-yl]phenyl}-N′-[4-(trifluoromethyl)-pyridin-2-yl]urea

EtOAc

NaHCO3

→

title compound

Ausbeute 33.3%

N-{4-[6-acetyl-4-amino-7-(morpholin-4-ylmethyl)pyrrolo[2,1-f][1,2,4]triazin-5-yl]phenyl}-N′-[4-(trifluoromethyl)-pyridin-2-yl]urea

Ausbeute 33.3%

Lösungsmittel

DMSO

H2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGto stir overnight
2. 2
   Sonstigethe next day the excess liquid was removed via pipette
3. 3
   workup.ADDITIONCareful addition of 5-10 mL of Et2O and 2 mL of CH2Cl2
4. 4
   Sonstigeprovided an off white suspension
5. 5
   FiltrationThis was filtered

Vorschrift

Dess-Martin periodinane (342.9 mg, 0.809 mmol) was added to a stirring solution of N-{4-[4-amino-6-(1-hydroxyethyl)-7-(morpholin-4-ylmethyl)pyrrolo[2,1-f][1,2,4]-triazin-5-yl]phenyl}-N′-[4-(trifluoromethyl)-pyridin-2-yl]urea (300 mg, 0.54 mmol) in DMSO (3 mL). The reaction was allowed to stir until complete by HPLC. Saturated aq. NaHCO3 solution (0.25 volumes) was added until a lot of solid had crashed out. Then 2 volumes of EtOAc and 0.5 volumes of H2O was added. This was allowed to stir overnight and the next day the excess liquid was removed via pipette. Careful addition of 5-10 mL of Et2O and 2 mL of CH2Cl2 provided an off white suspension. This was filtered to give a the title compound (100 mg, 0.18 mmol, 31% yield, 2 steps) as pure white powder. 1H-NMR (DMSO-d6). δ 10.20 (s, 1H), 10.04 (s, 1H), 8.67 (d, J=5.1 Hz, 1H), 8.20 (s, 1H), 8.10 (s, 1H), 7.78 (d, J=8.7 Hz, 2H), 7.52-7.48 (m, 3H), 4.19 (s, 2H), 3.63-3.60 (m, 4H), 2.56-2.53 (m, 4H), 2.19 (s, 3H). MS [M+H]+=555; LCMS RT=2.51 min.

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