Reaktion #73103

Reaktionsgleichung

Na2S2O4

(R)-8-cyclopentyl-7-ethyl-5-methyl-2-(pyridin-4-yl)-7,8-dihydropteridin-6(5H)-one

mCPBA

→

title compound

Ausbeute 6.4%

(R)-4-(8-cyclopentyl-7-ethyl-5-methyl-6-oxo-5,6,7,8-tetrahydropteridin-2-yl)pyridine 1-oxide

Ausbeute 6.4%

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.WAITat rt for another 3 hr
2. 2
   workup.STIRRINGstirred at r.t. for 30 min
3. 3
   ExtraktionThe mixture was extracted with DCM
4. 4
   Waschenwashed with saturated NaHCO3
5. 5
   Einengenconcentrated
6. 6
   Sonstigepurified by preparative HPLC

Vorschrift

To a solution of (R)-8-cyclopentyl-7-ethyl-5-methyl-2-(pyridin-4-yl)-7,8-dihydropteridin-6(5H)-one (Example 5, 300 mg, 0.89 mmol) in 25 mL of DCM at 0° C., mCPBA (306 mg, 1.79 mmol) was added and the mixture was stirred at 0° C. for 3 hr, then at rt for another 3 hr. Saturated Na2S2O4 was added and stirred at r.t. for 30 min. The mixture was extracted with DCM, washed with saturated NaHCO3, concentrated and purified by preparative HPLC to give the title compound as a yellow oil (20 mg, 6.4%). 1H NMR (CDCl3) δ: 8.47 (d, 2H), 8.38 (d, 2H) 8.06 (s, 1H), 4.51 (m, 1H), 4.38 (m, 1H), 3.42 (s, 3H), 2.2-1.7 (m, 10H) and 0.89 ppm (t, 3H); LCMS: 354.2 m/z (M+H)+; ret. Time: 1.79 min (Analytical Method E).

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