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

HRID 44825노트

반응식

HRID 44825 반응식
[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

참가 물질

5

반응물 3

HCID 24489Sodium DithioniteHCID 70297m-Chloroperbenzoic acidHCID 58405332HCID 58405332, 화합물

생성물 1

HCID 67253084(R)-4-(8-cyclopentyl-7-ethyl-5-methyl-6-oxo-5,6,7,8-tetrahydropteridin-2-yl)pyridine 1-oxide수율 6.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-ddd4ff251bf54cbabb009dba9dc90555
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541418B2

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