3,5-Dimethyl-4-hydroxybenzonitrile → 4-(2-amino-7-benzyl-7H-pyrrolo[2,3-d]pyrimidin-4-yloxy)-3,5-dimethyl-benzonitrile

HRID 1516822노트

반응식

HRID 1516822 반응식
[OH:1][C:2]1[C:9]([CH3:10])=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[CH3:11].[H-].[Na+].[CH2:14]([N:21]1[C:25]2[N:26]=[C:27]([NH2:31])[N:28]=[C:29](Cl)[C:24]=2[CH:23]=[CH:22]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN1C=CC=CC1=O>[NH2:31][C:27]1[N:28]=[C:29]([O:1][C:2]2[C:3]([CH3:11])=[CH:4][C:5]([C:6]#[N:7])=[CH:8][C:9]=2[CH3:10])[C:24]2[CH:23]=[CH:22][N:21]([CH2:14][C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:25]=2[N:26]=1

참가 물질

5

반응물 3

HCID 201763,5-Dimethyl-4-hydroxybenzonitrileHCID 24758Sodium hydrideHCID 105873407-benzyl-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-amine

생성물 1

HCID 576935754-(2-amino-7-benzyl-7H-pyrrolo[2,3-d]pyrimidin-4-yloxy)-3,5-dimethyl-benzonitrile수율 83%

시약·촉매·용매 1

HCID 127551-Methyl-2(1H)-pyridinone용매2회

실험 절차

To a solution of 4-hydroxy-3,5-dimethylbenzonitrile (1.62 mg, 11.0 mmol) in 1-methyl-2-pyridone (5 mL) in a sealed tube was added NaH (441 mg, 11.0 mmol). The reaction mixture was stirred at room temperature for 15 min and a solution of 7-benzyl-4-chloro-7H-pyrrolo[2,3-d]pyrimidin-2-ylamine (950 mg, 3.67 mmol) in 1-methyl-2-pyridone (5 mL) was added to the mixture. The mixture was heated at 150° C. for 16 h and cooled to room temperature. The reaction was poured into ice water and extracted with EtOAc (2×50 mL). The combined organic solution was washed with H2O (50 mL) and brine (50 mL), dried with Na2SO4, and concentrated to dryness. Silica gel chromatography (Hexanes:EtOAc=75:25) yielded 1.12 mg (83%) of 4-(2-amino-7-benzyl-7H-pyrrolo[2,3-d]pyrimidin-4-yloxy)-3,5-dimethyl-benzonitrile.

후처리

  1. temperatureThe mixture was heated at 150° C. for 16 h
  2. temperaturecooled to room temperature
  3. extractionextracted with EtOAc (2×50 mL)
  4. washThe combined organic solution was washed with H2O (50 mL) and brine (50 mL)
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated to dryness

출처 및 근거

ORD 기록
ord-d1f8828889b14cc59b26ef2bafa8f023
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08227601B2

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