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

HRID 426175노트

반응식

HRID 426175 반응식
[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

참가 물질

4

반응물 3

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

생성물 1

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

실험 절차

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).

후처리

  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))

출처 및 근거

ORD 기록
ord-7fe29f77de364449ad613905361a3345
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08106064B2

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