m-Toluidine → 4-Methyl-6-[(3-methylphenyl)amino]-2-(methylthio)-5-pyrimidinecarbonitrile

HRID 390048노트

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HRID 390048 반응식
Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH3:10])[N:5]=[C:4]([S:11][CH3:12])[N:3]=1.[CH3:13][C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][CH:20]=1)[NH2:17].C(N(C(C)C)CC)(C)C>CN(C=O)C>[CH3:10][C:6]1[C:7]([C:8]#[N:9])=[C:2]([NH:17][C:16]2[CH:18]=[CH:19][CH:20]=[C:14]([CH3:13])[CH:15]=2)[N:3]=[C:4]([S:11][CH3:12])[N:5]=1

참가 물질

5

반응물 3

HCID 7934m-ToluidineHCID 81531DiisopropylethylamineHCID 582963084-Chloro-6-methyl-2-(methylthio)pyrimidine-5-carbonitrile

생성물 1

HCID 582963344-Methyl-6-[(3-methylphenyl)amino]-2-(methylthio)-5-pyrimidinecarbonitrile수율 96%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
70 °C

실험 절차

To a solution of 4-chloro-6-methyl-2-(methylthio)-5-pyrimidinecarbonitrile (500 mg, 2.51 mmol) in DMF (6 mL) were added 3-methylaniline (322 mg, 3.01 mmol) and diisopropyl ethylamine (712 mg, 5.52 mmol), and the reaction mixture was stirred 70° C. for 1.5 h. The mixture was cooled and concentrated, and the residue was dissolved into EtOAc (30 mL) and washed with water (10 mL). The ethyl acetate extract was dried over Na2SO4, filtered, and concentrated. The residue was purified using column chromatography (silica gel, hexane/EtOAc, 0 to 100%) to give the product (650 mg, 96% yield).

후처리

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated
  3. dissolutionthe residue was dissolved into EtOAc (30 mL)
  4. washwashed with water (10 mL)
  5. extractionThe ethyl acetate extract
  6. dry with materialwas dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified

출처 및 근거

ORD 기록
ord-6f6868026b7247218587679230533392
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08383635B2

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