Potassium Carbonate → (4-Benzyl-pyrimidin-2-yl)-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine

HRID 1855326노트

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HRID 1855326 반응식
C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1.[CH3:26][O:27][C:28]1[CH:29]=[C:30]([NH2:40])[CH:31]=[CH:32][C:33]=1[N:34]1[CH:38]=[C:37]([CH3:39])[N:36]=[CH:35]1.[CH2:41]([C:48]1[CH:53]=[CH:52][N:51]=[C:50](Cl)[N:49]=1)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:41]([C:48]1[CH:53]=[CH:52][N:51]=[C:50]([NH:40][C:30]2[CH:31]=[CH:32][C:33]([N:34]3[CH:38]=[C:37]([CH3:39])[N:36]=[CH:35]3)=[C:28]([O:27][CH3:26])[CH:29]=2)[N:49]=1)[C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 183533314-Benzyl-2-chloro-pyrimidineHCID 454801813-methoxy-4-(4-methyl-1H-imidazol-1-yl)aniline

생성물 1

HCID 44192500(4-Benzyl-pyrimidin-2-yl)-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-amine수율 45%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 312751,4-Dioxane용매2회

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온도
20 °C

실험 절차

Palladium acetate (2.7 mg, 0.012 mmol) and 2-(dicyclohexylphosphino)-biphenyl (8.7 mg, 0.024 mmol) were dissolved under an atmosphere of nitrogen in dioxane (1 mL) and stirred for 10 min at 20° C. This solution was added at 20° C. under an atmosphere of nitrogen to a microwave flask containing 3-methoxy-4-(4-methyl-imidazol-1-yl)-phenylamine (61 mg, 0.3 mmol), 4-benzyl-2-chloro-pyrimidine (68 mg, 0.3 mmol) and potassium carbonate (829 mg, 6.0 mmol). The mixture was diluted with dioxane (1.7 mL) and heated for 30 min to 200° C. in a microwave oven. The reaction was poured onto water and extracted twice with ethyl acetate. The combined organic solutions were washed with brine, dried over sodium sulfate, filtered and the residue was purified by column chromatography on silica gel using dichloromethane/methanol (19:1 v/v) as eluent to yield the title compound (50 mg, 45%) as a yellow solid.

후처리

  1. additionThis solution was added at 20° C. under an atmosphere of nitrogen to a microwave flask
  2. temperatureheated for 30 min to 200° C. in a microwave oven
  3. additionThe reaction was poured onto water
  4. extractionextracted twice with ethyl acetate
  5. washThe combined organic solutions were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customthe residue was purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-c05ecf80ad3e4fd68661f3a294d171ce
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08962834B2

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