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Toluene → 3-(2-Chloro-6,7-dimethoxyquinazolin-4-yl)phenylamine

HRID 41489
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HRID 41489 반응식
[Cl:1][C:2]1[N:11]=[C:10](Cl)[C:9]2[C:4](=[CH:5][C:6]([O:15][CH3:16])=[C:7]([O:13][CH3:14])[CH:8]=2)[N:3]=1.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].[NH2:30][C:31]1[CH:32]=[C:33](B(O)O)[CH:34]=[CH:35][CH:36]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O1CCCC1>[Cl:1][C:2]1[N:11]=[C:10]([C:35]2[CH:36]=[C:31]([NH2:30])[CH:32]=[CH:33][CH:34]=2)[C:9]2[C:4](=[CH:5][C:6]([O:15][CH3:16])=[C:7]([O:13][CH3:14])[CH:8]=2)[N:3]=1
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참가 물질

7

반응물 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 922693-Aminophenylboronic acidHCID 5203272,4-Dichloro-6,7-dimethoxyquinazoline

생성물 1

HCID 576095393-(2-Chloro-6,7-dimethoxyquinazolin-4-yl)phenylamine수율 92.6%

시약·촉매·용매 2

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 8028Tetrahydrofuran용매

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온도
60 °C

실험 절차

Twenty-five grams of 2,4-dichloro-6,7-dimethoxyquinazoline was suspended in 2.25 L of a mixed solution consisting of toluene:tetrahydrofuran:a 2 N sodium carbonate solution=1:1:1. To the reaction mixture was added 21.5 g of 3-aminophenyl boronic acid ½ sulfate, and the mixture was degassed, the atmosphere in the reaction vessel was replaced with nitrogen. To the reaction mixture was added 2.23 g of tetrakis(triphenylphosphine)palladium(0), followed by stirring at 60° C. under a nitrogen atmosphere. Eighteen hours after initiation of the reaction, 1.2 g of tetrakis(triphenylphosphine)palladium(0) was added to the reaction mixture, and the stirring was continued. Thirty hours later, 1.2 g of tetrakis(triphenylphosphine)palladium(0) was further added to the reaction mixture, and stirring was further continued. Forty-eight hours after initiation of the reaction, the reaction mixture was cooled, and it was then transferred into a separatory funnel, so as to separate an organic layer. The obtained organic layer was washed with 300 mL of brine, and was then dried over anhydrous magnesium sulfate. The desiccant was removed by passing it through 250 g of silica gel. The silica gel was washed with 1.5 L of ethyl acetate, and the obtained organic layers were combined and concentrated to dryness. The residue was triturated with 200 mL of ethyl acetate, and the obtained solid was then filtrated. The solid was washed with 100 mL of diethyl ether and 200 mL of a mixed solution consisting of n-heptane:ethyl acetate=1:1, and dried under aeration to yield 28.2 g of a target product. Yield: 92.5%

후처리

  1. customthe mixture was degassed
  2. additionTo the reaction mixture was added 2.23 g of tetrakis(triphenylphosphine)palladium(0)
  3. customEighteen hours after initiation of the reaction, 1.2 g of tetrakis(triphenylphosphine)palladium(0)
  4. additionwas added to the reaction mixture
  5. stirringstirring
  6. customForty-eight hours after initiation of the reaction
  7. temperaturethe reaction mixture was cooled
  8. customit was then transferred into a separatory funnel
  9. customso as to separate an organic layer
  10. washThe obtained organic layer was washed with 300 mL of brine
  11. dry with materialwas then dried over anhydrous magnesium sulfate
  12. customThe desiccant was removed
  13. washThe silica gel was washed with 1.5 L of ethyl acetate
  14. concentrationconcentrated to dryness
  15. customThe residue was triturated with 200 mL of ethyl acetate
  16. filtrationthe obtained solid was then filtrated
  17. washThe solid was washed with 100 mL of diethyl ether and 200 mL of a mixed solution
  18. dry with materialethyl acetate=1:1, and dried under aeration

출처 및 근거

ORD 기록
ord-260a47ac49e14ba0a8195499016d1f09
출처 데이터셋
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08530654B2

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