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

HRID 44827노트

반응식

HRID 44827 반응식
[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

참가 물질

4

반응물 3

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

생성물 1

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

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-96c524a76cbd407f932587a45de61840
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541418B2

반응 노트

불러오는 중…