Ammonia → 4-Chloro-6-[2-(2-methoxy-ethoxy)-phenyl]-2-methyl-pyrimidine

HRID 1891011노트

반응식

HRID 1891011 반응식
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[N:17]=[C:16]([CH3:18])[NH:15][C:14](=O)[CH:13]=1.N.O=P(Cl)(Cl)[Cl:23]>>[Cl:23][C:14]1[CH:13]=[C:12]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][CH2:4][CH2:3][O:2][CH3:1])[N:17]=[C:16]([CH3:18])[N:15]=1

참가 물질

4

반응물 3

HCID 222AmmoniaHCID 24813Phosphorus oxychlorideHCID 1361275746-[2-(2-methoxy-ethoxy)-phenyl]-2-methyl-3H-pyrimidin-4-one

생성물 1

HCID 585505194-Chloro-6-[2-(2-methoxy-ethoxy)-phenyl]-2-methyl-pyrimidine수율 87%

반응 조건

온도
5 °C

실험 절차

A stirred suspension of 6-[2-(2-methoxy-ethoxy)-phenyl]-2-methyl-3H-pyrimidin-4-one (0.17 g, 0.66 mmol) in POCl3 (2 mL) was heated at reflux for 1 h. The reaction mixture was cooled to about 5° C. and poured cautiously into 10 ml ice-water, ammonia (10 mL) was added and extracted with ethyl acetate (2×10 mL), organic layers were combined, washed with water (5 mL) then dried over anhydrous sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (eluent CHCl3-EtOAc, 10:1), yielding 0.16 g (87%) 4-chloro-6-[2-(2-methoxy-ethoxy)-phenyl]-2-methyl-pyrimidine as colorless solid.

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 1 h
  3. additionwas added
  4. extractionextracted with ethyl acetate (2×10 mL), organic layers
  5. washwashed with water (5 mL)
  6. dry with materialthen dried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography on silica gel (eluent CHCl3-EtOAc, 10:1)

출처 및 근거

ORD 기록
ord-45efdde72e244b72b9c55f8ff043cd37
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08507498B2

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