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Dimethylformamide → 3-{3-[Cyano-(5-isopropyl-2,6-dimethoxy-pyrimidin-4-yl)-methyl]-5-methyl-phenyl}-acrylonitrile

HRID 426168
ノート
印刷プレビュー

反応式

HRID 426168 の反応式
Cl[C:2]1[C:7]([CH:8]([CH3:10])[CH3:9])=[C:6]([O:11][CH3:12])[N:5]=[C:4]([O:13][CH3:14])[N:3]=1.Br[CH2:16][C:17]1[CH:18]=[C:19]([CH:24]=[CH:25][C:26]#[N:27])[CH:20]=[C:21]([CH3:23])[CH:22]=1.[H-].[Na+].[Cl-].[NH4+].[CH3:32][N:33](C=O)C>>[C:32]([CH:16]([C:2]1[C:7]([CH:8]([CH3:10])[CH3:9])=[C:6]([O:11][CH3:12])[N:5]=[C:4]([O:13][CH3:14])[N:3]=1)[C:17]1[CH:18]=[C:19]([CH:24]=[CH:25][C:26]#[N:27])[CH:20]=[C:21]([CH3:23])[CH:22]=1)#[N:33]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 5

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 160881865-Isopropyl-6-chloro-2,4-dimethoxypyrimidineHCID 667054103-(3-Bromomethyl-5-methyl-phenyl)-acrylonitrile

生成物 1

HCID 667056503-{3-[Cyano-(5-isopropyl-2,6-dimethoxy-pyrimidin-4-yl)-methyl]-5-methyl-phenyl}-acrylonitrile
収率 16%

実験手順

To a stirred mixture of 4-chloro-5-isopropyl-2,6-dimethoxy-pyrimidine (7.12 g, 32.88 mmol) and 3-(3-bromomethyl-5-methyl-phenyl)-acrylonitrile (5.7 g, 31.21 mmol) in anhydrous DMF (60 ml) at 0° C. (ice bath) under nitrogen atmosphere, was portionwise added 60% sodium hydride (2.76 g, 68.88 mmol). After stirring for 1 hr., the mixture was further stirred at room temperature for overnight. The mixture was then neutralized with aqueous saturated ammonium chloride solution and the crude product was extracted with ether and purified by silica gel column chromatography (eluent, EA: hexanes (from 1:4 to 1:2)) to afford 1.8 g (16%) of a pale yellow foam. 1H NMR (300 MHz, CDCl3) δ 1.12 (3H, d, J=6.9 Hz), 1.15 (3H, d, J=6.9 Hz), 2.37 (3H, s), 3.02 (1H, m), 4.01 (6H, s), 5.39 (1H, s), 5.87 (1H, d, J=16.5 Hz), 7.23 (1H, s), 7.25 (1H, s), 7.27 (1H, s), 7.33 (1H, d, J=16.5 Hz).

後処理

  1. stirring, the mixture was further stirred at room temperature for overnight
  2. extractionthe crude product was extracted with ether
  3. custompurified by silica gel column chromatography (eluent, EA: hexanes (from 1:4 to 1:2))

出典と根拠

ORDレコード
ord-121e4c55bbf04429b888af7e32f8a2dc
出典データセット
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08106064B2

反応ノート

読み込み中…

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