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

HRID 1811899노트

반응식

HRID 1811899 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 516892Sodium Bicarbonate용매

반응 조건

온도
40 °C

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-94ea20e2e55d410b9eb69dc122b55254
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362241B2

반응 노트

불러오는 중…