Reaktion #2260049

Reaktionsgleichung

5-chloro-4-(3-methylpyridin-2-yl)-2-(methylsulfonyl)pyrimidine

5-chloro-4-(3-methylpyridin-2-yl)-2-(methylsulfinyl)pyrimidine

4-(methylsulfonylmethyl)piperidine

CsF

→

title compound

Ausbeute 46.0%

5-chloro-4-(3-methylpyridin-2-yl)-2-(4-(methylsulfonylmethyl)piperidin-1-yl)pyrimidine

Ausbeute 46.0%

Lösungsmittel

DMSO

MeOH

CH2Cl2

H2O

EtOAc

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe layers were separated
2. 2
   Extraktionthe aqueous layer was then extracted with EtOAc (30 mL×3)
3. 3
   WaschenThe combined organic layers were washed with brine (30 mL)
4. 4
   Trocknendried over Na2SO4
5. 5
   Filtrationfiltered
6. 6
   EinengenThe filtrate was concentrated
7. 7
   Sonstigethe residue was purified via prep

Vorschrift

To a mixture of 5-chloro-4-(3-methylpyridin-2-yl)-2-(methylsulfonyl)pyrimidine and 5-chloro-4-(3-methylpyridin-2-yl)-2-(methylsulfinyl)pyrimidine (300 mg, 1.05 mmol) in DMSO (15 mL) was added 4-(methylsulfonylmethyl)piperidine (440 mg, 1.65 mmol) and CsF (640 mg, 4.2 mmol). The resulting mixture was heated at 100° C. at microwave for 30 min. TLC (CH2Cl2:MeOH=10:1) indicated that the reaction was complete. The mixture was then treated with EtOAc (50 mL) and H2O (50 mL). The layers were separated and the aqueous layer was then extracted with EtOAc (30 mL×3). The combined organic layers were washed with brine (30 mL), dried over Na2SO4 and filtered. The filtrate was concentrated and the residue was purified via prep. HPLC to give title compound (183 mg, 46%) as a white solid. 1H NMR (400 MHz, CDCl3): δ 8.47-8.48 (d, 1H), 8.28 (s, 1H), 7.55-7.56 (dd, 1H), 7.20-7.24 (m, 1H), 4.66-4.69 (d, 1H), 2.88-2.92 (m, 7H), 2.30-2.34 (m, 1H), 2.18 (s, 3H), 1.94-1.97 (m, 2 H), 1.26-1.37 (m, 2H); m/z for C17H21ClN4O2S 381.4 (M+H)+.

Quelle