Reaktion #1453718

Reaktionsgleichung

[(2R)-3-(2-{2-chloro-6-[3-(dimethylamino)-2,2-dimethyl-1-pyrrolidinyl]-5-fluoro-4-pyrimidinyl}hydrazino)-2-(cyclopentylmethyl)-3-oxopropyl][(phenylmethyl)oxy]formamide

→

[(2R)-3-(2-{2-chloro-6-[3-(dimethylamino)-2,2-dimethyl-1-pyrrolidinyl]-5-fluoro-4-pyrimidinyl}hydrazino)-2-(cyclopentylmethyl)-3-oxopropyl]hydroxyformamide

Ausbeute 46.0%

Lösungsmittel

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas hydrogenated at 50 psi overnight
2. 2
   Filtrationwas then filtered through a 0.2 μM membrane
3. 3
   Einengenconcentrated in vacuo
4. 4
   workup.ADDITIONTo a solution of the residue in MeOH (4 mL) was added 20% Pd(OH)2/C (50% water, 5 mg)
5. 5
   FiltrationThe mixture was then filtered though a 0.2 μM membrane
6. 6
   Einengenthe solution was concentrated in vacuo
7. 7
   SonstigeThe residue was purified by Gilson RPLC

Vorschrift

To a solution of [(2R)-3-(2-{2-chloro-6-[3-(dimethylamino)-2,2-dimethyl-1-pyrrolidinyl]-5-fluoro-4-pyrimidinyl}hydrazino)-2-(cyclopentylmethyl)-3-oxopropyl][(phenylmethyl)oxy]formamide (0.1737 g, 0.294 mmol) in MeOH (10 mL) was added 5% Rh/C (175 mg). The mixture was hydrogenated at 50 psi overnight, and was then filtered through a 0.2 μM membrane and concentrated in vacuo. To a solution of the residue in MeOH (4 mL) was added 20% Pd(OH)2/C (50% water, 5 mg). The mixture was hydrogenated under balloon pressure for 50 min. The mixture was then filtered though a 0.2 μM membrane, and the solution was concentrated in vacuo. The residue was purified by Gilson RPLC to give [(2R)-3-(2-{2-chloro-6-[3-(dimethylamino)-2,2-dimethyl-1-pyrrolidinyl]-5-fluoro-4-pyrimidinyl}hydrazino)-2-(cyclopentylmethyl)-3-oxopropyl]hydroxyformamide (0.0670 g, 46% yield, mixture of diastereomers) as a while solid following crystallization from EtOAc-hexanes. LCMS: (M+H)+: 500.3.

Quelle