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Cesium carbonate → 5-(3-(9-(4-methoxybenzyl)-9H-purin-6-yl)pyridin-2-yloxy)-6-methylisoquinolin-1(2H)-one

HRID 1042280
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HRID 1042280 반응식
[CH3:1][O:2][C:3]1[CH:25]=[CH:24][C:6]([CH2:7][N:8]2[CH:16]=[N:15][C:14]3[C:9]2=[N:10][CH:11]=[N:12][C:13]=3[C:17]2[C:18](F)=[N:19][CH:20]=[CH:21][CH:22]=2)=[CH:5][CH:4]=1.[OH:26][C:27]1[C:36]([CH3:37])=[CH:35][CH:34]=[C:33]2[C:28]=1[CH:29]=[CH:30][NH:31][C:32]2=[O:38].C(=O)([O-])[O-].[Cs+].[Cs+]>CN1C(=O)CCC1>[CH3:1][O:2][C:3]1[CH:25]=[CH:24][C:6]([CH2:7][N:8]2[CH:16]=[N:15][C:14]3[C:9]2=[N:10][CH:11]=[N:12][C:13]=3[C:17]2[C:18]([O:26][C:27]3[C:36]([CH3:37])=[CH:35][CH:34]=[C:33]4[C:28]=3[CH:29]=[CH:30][NH:31][C:32]4=[O:38])=[N:19][CH:20]=[CH:21][CH:22]=2)=[CH:5][CH:4]=1
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참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 589422595-hydroxy-6-methylisoquinolin-1(2H)-oneHCID 59627379HCID 59627379, 화합물

생성물 1

HCID 687236525-(3-(9-(4-methoxybenzyl)-9H-purin-6-yl)pyridin-2-yloxy)-6-methylisoquinolin-1(2H)-one수율 51%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

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온도
130 °C

실험 절차

A mixture of 9-(4-methoxybenzyl)-6-(2-fluoropyridin-3-yl)-9H-purine (0.48 g, 1.4 mmol), 5-hydroxy-6-methylisoquinolin-1(2H)-one (0.25 g, 1.4 mmol) and cesium carbonate (1.1 g, 3.3 mmol) in NMP (5 mL) was stirred and heated in a Discover® model microwave reactor (CEM, Matthews, N.C.) at 130° C. for 60 min (100 watts, Powermax feature on, ramp time 1 min) The crude reaction mixture was partitioned between 3:1 CHCl3:IPA (100 mL) and water (150 mL). The aqueous phase was extracted with 3:1 CHCl3:IPA (50 mL). The combined organic extracts were washed with 1 N NaOH (2×75 mL), water (2×75 mL), satd NaCl (50 mL), dried over Na2SO4, filtered, and concentrated in vacuo to give a viscous brown oil which was chromatographed through a Redi-Sep® pre-packed silica gel column (80 g), eluting with a gradient of 1% to 7% MeOH in CH2Cl2, to provide 5-(3-(9-(4-methoxybenzyl)-9H-purin-6-yl)pyridin-2-yloxy)-6-methylisoquinolin-1(2H)-one (0.35 g, 51% yield) as a white solid. MS (ESI, pos. ion) m/z: 491.2 [M+H]+.

후처리

  1. customreaction mixture
  2. customwas partitioned between 3:1 CHCl3
  3. extractionThe aqueous phase was extracted with 3:1 CHCl3
  4. washThe combined organic extracts were washed with 1 N NaOH (2×75 mL), water (2×75 mL), satd NaCl (50 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a viscous brown oil which
  9. customwas chromatographed through a Redi-Sep® pre-packed silica gel column (80 g)
  10. washeluting with a gradient of 1% to 7% MeOH in CH2Cl2

출처 및 근거

ORD 기록
ord-bbf89072c92d4f41ac0972104fc78440
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08557830B2

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