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Sodium hydride → 5-[Cyano-(5-isopropyl-2,6-dimethoxy-pyrimidin-4-yl)-methyl]-isophthalonitrile

HRID 426278
ノート
印刷プレビュー

反応式

HRID 426278 の反応式
[C:1]([CH2:3][C:4]1[CH:5]=[C:6]([C:12]#[N:13])[CH:7]=[C:8]([CH:11]=1)[C:9]#[N:10])#[N:2].Cl[C:15]1[C:20]([CH:21]([CH3:23])[CH3:22])=[C:19]([O:24][CH3:25])[N:18]=[C:17]([O:26][CH3:27])[N:16]=1.[H-].[Na+]>CN(C=O)C>[C:1]([CH:3]([C:15]1[C:20]([CH:21]([CH3:23])[CH3:22])=[C:19]([O:24][CH3:25])[N:18]=[C:17]([O:26][CH3:27])[N:16]=1)[C:4]1[CH:11]=[C:8]([C:9]#[N:10])[CH:7]=[C:6]([CH:5]=1)[C:12]#[N:13])#[N:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 160881865-Isopropyl-6-chloro-2,4-dimethoxypyrimidineHCID 667055675-Cyanomethyl-isophthalonitrile

生成物 1

HCID 591847545-[Cyano-(5-isopropyl-2,6-dimethoxy-pyrimidin-4-yl)-methyl]-isophthalonitrile収率 43%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

5-Cyanomethyl-isophthalonitrile (0.285 g, 1.70 mmol) and 4-chloro-5-isopropyl-2,6-dimethoxy-pyrimidine (0.360 g, 1.66 mmol) was dissolved in DMF (8.0 mL) and cooled to 0° C. 60% Sodium hydride (0.136 g, 3.40 mmol) was added portionwise and the reaction was stirred at 0° C. for 2 h, then rt overnight. The reaction was quenched with saturated ammonium chloride solution and pH was adjusted to ˜6.0 with 1N HCl. Mixture was extracted with ethyl acetate and organic layer was dried (MgSO4) and concentrated. The resulting residue was purified by flash column chromatography (silica gel, 10 to 50% ethyl acetate/hexane) to give a white solid (0.2457 g, 43%). 1H NMR (300 MHz, CDCl3): δ 7.90 (s, 3H), 5.46 (s, 1H), 3.96 (s, 3H), 3.89 (s, 3H), 3.05-2.9 (m, 1H), 1.16 (d, J=6.9 Hz, 3H), 1.15 (d, J=7.2 Hz, 3H).

後処理

  1. customrt overnight
  2. customThe reaction was quenched with saturated ammonium chloride solution and pH
  3. extractionMixture was extracted with ethyl acetate and organic layer
  4. dry with materialwas dried (MgSO4)
  5. concentrationconcentrated
  6. customThe resulting residue was purified by flash column chromatography (silica gel, 10 to 50% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-6fc24924f44c46e9b752ce10f90c2dc6
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

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート