Reaktion #2179484

Reaktionsgleichung

6-methyl-N1-(3-(methylthio)phenyl)-N5-(3-(pyrimidin-4-yl)pyridin-2-yl)isoquinoline-1,5-diamine

THF

oxone

→

6-methyl-N1-(3-(methylsulfonyl)phenyl)-N5-(3-(pyrimidin-4-yl)pyridin-2-yl)isoquinoline-1,5-diamine

Lösungsmittel

MeOH

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe resulting cloudy reaction mixture
2. 2
   Temperaturwarming slowly to ˜10° C.) for 3 h
3. 3
   SonstigeThe reaction mixture was quenched at 0° C. by the addition of satd aq Na2SO3 (100 mL)
4. 4
   workup.STIRRINGstirred at that temperature for 15 min
5. 5
   EinengenThe mixture was concentrated in vacuo
6. 6
   Sonstigeto remove THF
7. 7
   Extraktionthe remaining aqueous mixture was extracted with 3:1 CHCl3
8. 8
   ExtraktionThe organic extract
9. 9
   Waschenwas washed with saturated aqueous NaCl (50 mL)
10. 10
    Trocknendried over Na2SO4
11. 11
    Filtrationfiltered
12. 12
    Einengenconcentrated in vacuo
13. 13
    Sonstigeto afford a yellow solid
14. 14
    Sonstigechromatographed through a Redi-Sep® pre-packed silica gel column (40 g)
15. 15
    Wascheneluting with a gradient of 1% to 8% MeOH in CH2Cl2

Vorschrift

A solution of 6-methyl-N1-(3-(methylthio)phenyl)-N5-(3-(pyrimidin-4-yl)pyridin-2-yl)isoquinoline-1,5-diamine (0.250 g, 0.555 mmol) in THF (30 mL) and MeOH (20 mL) was stirred in an ice bath and treated with a solution of oxone® (0.750 g, 1.22 mmol) in water (10 mL). The resulting cloudy reaction mixture was stirred at 0° C. (warming slowly to ˜10° C.) for 3 h. The reaction mixture was quenched at 0° C. by the addition of satd aq Na2SO3 (100 mL) and stirred at that temperature for 15 min. The mixture was concentrated in vacuo to remove THF and the remaining aqueous mixture was extracted with 3:1 CHCl3:IPA (3×100 mL). The organic extract was washed with saturated aqueous NaCl (50 mL), dried over Na2SO4, filtered, and concentrated in vacuo to afford a yellow solid. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Redi-Sep® pre-packed silica gel column (40 g), eluting with a gradient of 1% to 8% MeOH in CH2Cl2, to provide 6-methyl-N1-(3-(methylsulfonyl)phenyl)-N5-(3-(pyrimidin-4-yl)pyridin-2-yl)isoquinoline-1,5-diamine. MS (M+H)+ 483.5.

Quelle