Sodium Hydroxide → [9-Methoxy-1-(2-methoxy-4,6-dimethylpyrimidin-5-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]methanol

HRID 1629019노트

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HRID 1629019 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([C:32](OC)=[O:33])=[C:13]2[C:17]=1[N:16]=[C:15]1[N:18]([C:22]3[C:23]([CH3:31])=[N:24][C:25]([O:29][CH3:30])=[N:26][C:27]=3[CH3:28])[CH2:19][CH2:20][CH2:21][N:14]21.[OH-].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>O1CCCC1.O>[CH3:7][O:8][C:9]1[C:17]2[N:16]=[C:15]3[N:18]([C:22]4[C:23]([CH3:31])=[N:24][C:25]([O:29][CH3:30])=[N:26][C:27]=4[CH3:28])[CH2:19][CH2:20][CH2:21][N:14]3[C:13]=2[C:12]([CH2:32][OH:33])=[CH:11][CH:10]=1

참가 물질

7

반응물 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 21226445Aluminium lithium hydrideHCID 57785995Methyl 9-methoxy-1-(2-methoxy-4,6-dimethylpyrimidin-5-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carboxylate

생성물 1

HCID 57786030[9-Methoxy-1-(2-methoxy-4,6-dimethylpyrimidin-5-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazol-6-yl]methanol수율 71.3%

시약·촉매·용매 2

HCID 962Water용매2회HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

To a suspension of lithium aluminum hydride (0.14 g, 3.69 mmol) in tetrahydrofuran (10 mL) was added dropwise a solution of methyl 9-methoxy-1-(2-methoxy-4,6-dimethylpyrimidin-5-yl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carboxylate (720 mg, 1.81 mmol) in tetrahydrofuran (30 mL) at 0° C. After stirring at 0° C. for 1 hr, water (0.14 mL), 15% aqueous sodium hydroxide (0.14 mL) and water (0.42 mL) were successively added dropwise to the reaction mixture at 0° C. The mixture was stirred at room temperature for 4 hr and anhydrous magnesium sulfate was added to the mixture. The solid was removed by filtration. The filtrate was concentrated in vacuo and the residue was purified by flash column chromatography on silica gel eluting with a 5-25% methanol/ethyl acetate gradient mixture to give the title compound as a colorless solid (478 mg, 1.29 mmol, 71%).

후처리

  1. stirringThe mixture was stirred at room temperature for 4 hr
  2. customThe solid was removed by filtration
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was purified by flash column chromatography on silica gel eluting with a 5-25% methanol/ethyl acetate gradient mixture

출처 및 근거

ORD 기록
ord-c7d0affc4e954c3b8c94a5ca959067f3
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785460B2

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