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

Reaktionsgleichung

[CH:1]1([N:6]2[C:15]3[N:14]=[C:13]([C:16]4[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=4)[N:12]=[CH:11][C:10]=3[N:9]([CH3:22])[C:8](=[O:23])[C@H:7]2[CH2:24][CH3:25])[CH2:5][CH2:4][CH2:3][CH2:2]1.C1C=C(Cl)C=C(C(OO)=[O:34])C=1.[O-]S(S([O-])=O)=O.[Na+].[Na+]>C(Cl)Cl>[CH:1]1([N:6]2[C:15]3[N:14]=[C:13]([C:16]4[CH:21]=[CH:20][N+:19]([O-:34])=[CH:18][CH:17]=4)[N:12]=[CH:11][C:10]=3[N:9]([CH3:22])[C:8](=[O:23])[C@H:7]2[CH2:24][CH3:25])[CH2:2][CH2:3][CH2:4][CH2:5]1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

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).

Aufarbeitung

waitat rt for another 3 hr
stirringstirred at r.t. for 30 min
extractionThe mixture was extracted with DCM
washwashed with saturated NaHCO3
concentrationconcentrated
custompurified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag: ord-ddd4ff251bf54cbabb009dba9dc90555
Quelldatensatz: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08541418B2

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