Reaction #73103

Reaction equation

Na2S2O4

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

mCPBA

→

title compound

Yield 6.4%

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

Yield 6.4%

Solvents

DCM

Conditions

Workup

1. 1
   workup.WAITat rt for another 3 hr
2. 2
   workup.STIRRINGstirred at r.t. for 30 min
3. 3
   ExtractionThe mixture was extracted with DCM
4. 4
   Washwashed with saturated NaHCO3
5. 5
   Concentrationconcentrated
6. 6
   Otherpurified by preparative HPLC

Procedure

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).

Source