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

HRID 44827ノート

反応式

HRID 44827 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]=[C:18](F)[CH:17]=4)[N:12]=[CH:11][C:10]=3[N:9]([CH3:23])[C:8](=[O:24])[C@H:7]2[CH2:25][CH3:26])[CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-:27].[Na+].[CH3:29]O>>[CH:1]1([N:6]2[C:15]3[N:14]=[C:13]([C:16]4[CH:21]=[CH:20][N:19]=[C:18]([O:27][CH3:29])[CH:17]=4)[N:12]=[CH:11][C:10]=3[N:9]([CH3:23])[C:8](=[O:24])[C@H:7]2[CH2:25][CH3:26])[CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

4

反応物 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 58405345(R)-8-cyclopentyl-7-ethyl-2-(2-fluoropyridin-4-yl)-5-methyl-7,8-dihydropteridin-6(5H)-one

生成物 1

HCID 58405706(R)-8-cyclopentyl-7-ethyl-2-(2-methoxypyridin-4-yl)-5-methyl-7,8-dihydropteridin-6(5H)-one収率 60%

実験手順

To a solution of (R)-8-cyclopentyl-7-ethyl-2-(2-fluoropyridin-4-yl)-5-methyl-7,8-dihydropteridin-6(5H)-one (Example 16, 200 mg, 0.56 mmol) in 3 mL of CH3OH, aqueous NaOH (1.4 mL of 2N, 2.8 mmol) was added, the mixture was heated to reflux overnight, concentrated under reduced pressure, then extracted with EtOAc. The combined organic phase was dried with Na2SO4, concentrated under reduced pressure and chromagraphed (PE:EA=1:1) to give the title compound as a yellow solid (120 mg, 60% yield). 1H NMR (CDCl3) δ: 8.25 (d, 1H), 7.97 (s, 1H) 7.76 (m, 1H), 7.64 (s, 1H), 4.47 (m, 1H), 4.31 (m, 1H), 4.0 (s, 3H), 3.39 (s, 3H), 2.2-1.6 (m, 10H) and 0.88 ppm (t, 3H); LCMS: 368.2 m/z (M+H)+; ret. Time: 1.77 min (Analytical Method E).

後処理

  1. temperaturethe mixture was heated
  2. temperatureto reflux overnight
  3. concentrationconcentrated under reduced pressure
  4. extractionextracted with EtOAc
  5. dry with materialThe combined organic phase was dried with Na2SO4
  6. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-96c524a76cbd407f932587a45de61840
出典データセット
uspto-grants-2013_09
特許番号
US08541418B2

反応ノート

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