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

HRID 1508672ノート

反応式

HRID 1508672 の反応式
[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

参加物

5

反応物 4

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

生成物 1

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

反応条件

温度
100 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-b0c5a58b201d4af0971f44a04f5b87fb
出典データセット
uspto-grants-2015_12
特許番号
US09221843B2

反応ノート

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