N,N-Diethylaniline → 2,5-Dichloro-4,6-dimethylpyrimidine

HRID 1193118ノート

反応式

HRID 1193118 の反応式
[Cl:1][C:2]1[C:3]([CH3:10])=[N:4][C:5](O)=[N:6][C:7]=1[CH3:8].O=P(Cl)(Cl)[Cl:13].N(C1C=CC=CC=1)(CC)CC>>[Cl:13][C:5]1[N:4]=[C:3]([CH3:10])[C:2]([Cl:1])=[C:7]([CH3:8])[N:6]=1

参加物

4

反応物 3

HCID 7061N,N-DiethylanilineHCID 24813Phosphorus oxychlorideHCID 178433498HCID 178433498、化合物

生成物 1

HCID 138809112,5-Dichloro-4,6-dimethylpyrimidine収率 83%

反応条件

温度
125 °C

実験手順

To 5-chloro-4,6-dimethylpyrimidin-2-ol (992 mg, 6.26 mmol) was added POCl3 (2.22 mL, 23.77 mmol) followed by Et2NPh (0.75 mL, 4.69 mmol) dropwise. The mixture was heated at 125° C. for 2 h. At approximately 2 h the reaction became homogeneous and was checked by HPLC and it showed all starting material had been consumed. The mixture was allowed to cool to room temperature and was then added dropwise to ice. After the ice had melted there was a white solid in a pink liquid. The aqueous layer was extracted with DCM and the combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. Chromatography (Hex to 10% EtOAc/Hex) afforded the desired product as a white solid (915 mg, 83%). 1H NMR (500 MHz, CDCl3): 2.57 (s, 6H).

後処理

  1. customhad been consumed
  2. temperatureto cool to room temperature
  3. additionwas then added dropwise to ice
  4. extractionThe aqueous layer was extracted with DCM
  5. dry with materialthe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-e043f876d1bc4a1f9e2416cd7408be1e
出典データセット
uspto-grants-2014_03
特許番号
US08680275B2

反応ノート

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