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

HRID 1524920노트

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HRID 1524920 반응식
[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

참가 물질

4

반응물 3

HCID 7061N,N-DiethylanilineHCID 24813Phosphorus oxychlorideHCID 178433498HCID 178433498, 화합물

생성물 1

HCID 138809112,5-Dichloro-4,6-dimethylpyrimidine수율 83%

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온도
125 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-d9cb65f05665445bb96266f4badb18c7
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09079911B2

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