Sodium Hydroxide → 4-Chloro-2-(3-chlorophenyl)-6-ethylpyrimidine

HRID 1508672노트

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HRID 1508672 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[NH:13][C:12](=O)[CH:11]=[C:10]([CH2:15][CH3:16])[N:9]=2)[CH:5]=[CH:6][CH:7]=1.O=P(Cl)(Cl)[Cl:19].C([O-])(O)=O.[Na+].[OH-].[Na+]>>[Cl:19][C:12]1[CH:11]=[C:10]([CH2:15][CH3:16])[N:9]=[C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)[N:13]=1

참가 물질

5

반응물 4

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 1356311952-(3-chlorophenyl)-6-ethylpyrimidin-4(3H)-one

생성물 1

HCID 435575804-Chloro-2-(3-chlorophenyl)-6-ethylpyrimidine수율 99%

반응 조건

온도
100 °C

실험 절차

A 250-mL round bottom flask was charged with 2-(3-chlorophenyl)-6-ethylpyrimidin-4(3H)-one (9.3 g, 39.8 mmol, 1 eq.). POCl3 (50 mL, 536 mmol, 13.4 eq.) was cautiously added at 0° C. The resulting mixture was stirred at 100° C. for 5 hr. After cooling to room temperature, the mixture was added slowly dropwise to cold aq. NaHCO3. NaOH was added to keep the pH˜0.7 during quenching. The mixture was extracted with ethyl acetate. The organic extract was dried over sodium sulfate, filtered and concentrated under reduced pressure. Purification by silica gel chromatography using dichloromethane/ethyl acetate as eluent afforded 4-chloro-2-(3-chlorophenyl)-6-ethylpyrimidine (9.3 g, 99% yield) as a white solid. 1H NMR (CD3OD, 500 MHz) δ 8.32 (s, 1H), 8.28 (d, J=7.5 Hz, 1H), 7.50-7.46 (m, 1H), 7.45-7.40 (m, 1H), 7.27 (s, 1H), 2.83 (q, J=7.5 Hz, 2H), 1.34 (t, J=7.5 Hz, 3H).

후처리

  1. temperatureAfter cooling to room temperature
  2. customduring quenching
  3. extractionThe mixture was extracted with ethyl acetate
  4. extractionThe organic extract
  5. dry with materialwas dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customPurification by silica gel chromatography

출처 및 근거

ORD 기록
ord-b0c5a58b201d4af0971f44a04f5b87fb
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221843B2

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