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

HRID 2093682ノート

反応式

HRID 2093682 の反応式
[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

参加物

5

反応物 3

HCID 24489Sodium DithioniteHCID 70297m-Chloroperbenzoic acidHCID 58405332HCID 58405332、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d75998137ab647e0a5240603356adf5c
出典データセット
uspto-grants-2013_05
特許番号
US08445503B2

反応ノート

読み込み中…