1,2-Dimethoxyethane → HCID 59840903, 화합물

HRID 1890972노트

반응식

HRID 1890972 반응식
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[CH:4][N:3]=1.[CH2:9]([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1B(O)O)[CH3:10].C(COC)OC.C([O-])(O)=O.[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[Cl:1][C:2]1[CH:7]=[C:6]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[O:11][CH2:9][CH3:10])[N:5]=[CH:4][N:3]=1

참가 물질

7

반응물 4

HCID 80711,2-DimethoxyethaneHCID 709434,6-DichloropyrimidineHCID 516892Sodium BicarbonateHCID 2734902(2-Ethoxyphenyl)boronic acid

생성물 1

HCID 59840903HCID 59840903, 화합물

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매

실험 절차

To a solution of 4,6-dichloropyrimidine (6.0 g, 0.04 mol) and 2-ethoxyphenylboronic acid (4.81 g, 0.029 mol) in mixture of dimethoxyethane (120 mL) and water (18 mL) were added NaHCO3 (6.72 g, 0.08 mol) and (PPh3)2PdCl2 (0.84 g) and the reaction mixture was allowed to reflux for 8 h, then it was concentrated under reduced pressure. The residue was dissolved in CH2Cl2 (100 mL), the resulting solution was washed with water (20 mL), dried over anhydrous K2CO3, filtered and the solvent removed under reduced pressure. The crude product was purified by flash chromatography on silica (eluent CH2Cl2) and recrystallized from hexanes. Yield of 4-chloro-6-(2-ethoxyphenyl)-pyrimidine 4.97 g (73%).

후처리

  1. temperatureto reflux for 8 h
  2. concentrationit was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in CH2Cl2 (100 mL)
  4. washthe resulting solution was washed with water (20 mL)
  5. dry with materialdried over anhydrous K2CO3
  6. filtrationfiltered
  7. customthe solvent removed under reduced pressure
  8. customThe crude product was purified by flash chromatography on silica (eluent CH2Cl2)
  9. customrecrystallized from hexanes

출처 및 근거

ORD 기록
ord-e021442e31e941d4b229242b536ecb63
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08507498B2

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