Pyridine → n-(6-chloro-2-methylpyrimidin-4-yl)acetamide

HRID 1811899ノート

反応式

HRID 1811899 の反応式
[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH2:9])[CH:3]=1.N1C=CC=CC=1.[C:16](OC(=O)C)(=[O:18])[CH3:17]>C([O-])(O)=O.[Na+]>[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([NH:9][C:16](=[O:18])[CH3:17])[CH:3]=1

参加物

5

反応物 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 2867546-Chloro-2-methylpyrimidin-4-amine

生成物 1

HCID 243561n-(6-chloro-2-methylpyrimidin-4-yl)acetamide収率 71%

試薬・触媒・溶媒 1

HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
40 °C

実験手順

A mixture of 6-chloro-2-methylpyrimidin-4-amine (500 mg, 3483 μmol), pyridine (568 μl, 6965 μmol), and acetic anhydride (493 μl, 5224 μmol) was stirred at 40° C. for 24 h. The mixture was cooled down to rt. The reaction mixture was diluted with saturated NaHCO3 (30 mL) and extracted with EtOAc (2×40 mL). The organic extract was washed with saturated NaCl (about2 mL), dried over Na2SO4, filtered, concentrated in vacuo and the residue was purified by silica gel chromatography eluting with 40% EtOAc/hexanes to give N-(6-chloro-2-methylpyrimidin-4-yl)acetamide (458 mg, 71% yield). 1H NMR (300 MHz, CDCl3) δ 8.03 (s, 1H); 7.90 (s, 1H); 2.58 (s, 3H); 2.23 (s, 3H). m/z (ESI, +ve ion) 186 (M+H)+.

後処理

  1. temperatureThe mixture was cooled down to rt
  2. extractionextracted with EtOAc (2×40 mL)
  3. extractionThe organic extract
  4. washwas washed with saturated NaCl (about2 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customthe residue was purified by silica gel chromatography
  9. washeluting with 40% EtOAc/hexanes

出典と根拠

ORDレコード
ord-94ea20e2e55d410b9eb69dc122b55254
出典データセット
uspto-grants-2013_01
特許番号
US08362241B2

反応ノート

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