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

HRID 426175ノート

反応式

HRID 426175 の反応式
[CH3:1][O:2][CH:3]([O:27][CH3:28])[C:4]1[CH:5]=[C:6]([CH:11]([C:14]2[C:19]([CH:20]([CH3:22])[CH3:21])=[C:18]([O:23][CH3:24])[N:17]=[C:16]([O:25][CH3:26])[N:15]=2)C#N)[CH:7]=[C:8]([CH3:10])[CH:9]=1.[H-].[Na+].CN(C=[O:35])C>>[CH3:1][O:2][CH:3]([O:27][CH3:28])[C:4]1[CH:5]=[C:6]([C:11]([C:14]2[C:19]([CH:20]([CH3:22])[CH3:21])=[C:18]([O:23][CH3:24])[N:17]=[C:16]([O:25][CH3:26])[N:15]=2)=[O:35])[CH:7]=[C:8]([CH3:10])[CH:9]=1

参加物

4

反応物 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 59184766(3-Dimethoxymethyl-5-methyl-phenyl)-(5-isopropyl-2,6-dimethoxy-pyrimidin-4-yl)-acetonitrile

生成物 1

HCID 59184803(3-Dimethoxymethyl-5-methyl-phenyl)-(5-isopropyl-2,6-dimethoxy-pyrimidin-4-yl)-methanone収率 98%

実験手順

To a stirred solution of (3-dimethoxymethyl-5-methyl-phenyl)-(5-isopropyl-2,6-dimethoxy-pyrimidin-4-yl)-acetonitrile (3.4 g, 8.8 mmol) in anhydrous DMF (36 ml) at room temperature under nitrogen atmosphere, was added 60% sodium hydride (0.423 g, 10.6 mmol). After 20 min., oxygen was bubbled into the mixture for 3 hr. The mixture was then partitioned between ether and water, The ether layer was taken, washed with water twice, dried with anhydrous magnesium sulfate, filtered, and evaporated in vacuo. The residue was purified by silica gel column chromatography (eluent, EA:hexanes (1:4)) to afford 3.26 g (98%) of a pale yellow solid. m.p. 86-88° C.; 1H NMR (300 MHz, CDCl3) δ 1.22 (6H, d, J=6.3 Hz), 2.41 (3H, s), 2.81 (1H, m), 3.31 (6H, s), 3.93 (3H, s), 4.06 (3H, s), 5.36 (1H, s), 7.53 (1H, s), 7.64 (1H, s), 7.71 (1H, s).

後処理

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

出典と根拠

ORDレコード
ord-7fe29f77de364449ad613905361a3345
出典データセット
uspto-grants-2012_01
特許番号
US08106064B2

反応ノート

読み込み中…