Dimethylformamide → (3,5-Dichloro-phenyl)-(5-isopropyl-2,6-dimethoxy-pyrimidin-4-yl)-methanone

HRID 426133ノート

反応式

HRID 426133 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([C:12]2[C:17]([CH:18]([CH3:20])[CH3:19])=[C:16]([O:21][CH3:22])[N:15]=[C:14]([O:23][CH3:24])[N:13]=2)C#N)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[H-].[Na+].CN(C=[O:31])C>>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([C:12]2[C:17]([CH:18]([CH3:20])[CH3:19])=[C:16]([O:21][CH3:22])[N:15]=[C:14]([O:23][CH3:24])[N:13]=2)=[O:31])[CH:5]=[C:6]([Cl:8])[CH:7]=1

参加物

4

反応物 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 59184725(3,5-Dichloro-phenyl)-(5-isopropyl-2,6-dimethoxy-pyrimidin-4-yl)-acetonitrile

生成物 1

HCID 59184648(3,5-Dichloro-phenyl)-(5-isopropyl-2,6-dimethoxy-pyrimidin-4-yl)-methanone収率 80%

実験手順

To a stirred solution of (59) (9.6 g, 26 mmol) in anhydrous DMF (100 ml) under nitrogen atmosphere, was added 60% sodium hydride (1.05 g, 26 mmol). After 10 min., oxygen was bubbled into the reaction mixture for 4 hr. The mixture was partitioned between ether and aqueous saturated ammonium chloride solution. The organic layer was taken, washed with water twice, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo. The residue was then purified by silica gel column chromatography (eluent, ether:hexanes (1:10)) to afford 7.36 g (80%) of the title compound as a white solid. m.p. 120-121° C.; 1H NMR (200 MHz, CDCl3) δ 1.22 (6H, d, J=7.0 Hz), 2.86 (1H, m), 3.96 (6H, s), 4.09 (3H, s), 7.60-7.74 (3H, m).

後処理

  1. customoxygen was bubbled into the reaction mixture for 4 hr
  2. customThe mixture was partitioned between ether and aqueous saturated ammonium chloride solution
  3. washwashed with water twice
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was then purified by silica gel column chromatography (eluent, ether:hexanes (1:10))

出典と根拠

ORDレコード
ord-adb5ff45f1814e4eb84830f1ce00397f
出典データセット
uspto-grants-2012_01
特許番号
US08106064B2

反応ノート

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