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 1629019ノート

反応式

HRID 1629019 の反応式
[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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-c7d0affc4e954c3b8c94a5ca959067f3
出典データセット
uspto-grants-2014_07
特許番号
US08785460B2

反応ノート

読み込み中…