Sodium hydride → 2-chloro-4-(4-cyclopropyl-2,6-dimethylphenoxy)-7H-pyrrolo[2,3-d]pyrimidine

HRID 1516830노트

반응식

HRID 1516830 반응식
[CH:1]1([C:4]2[CH:9]=[C:8]([CH3:10])[C:7]([OH:11])=[C:6]([CH3:12])[CH:5]=2)[CH2:3][CH2:2]1.[H-].[Na+].[Cl:15][C:16]1[N:17]=[C:18](Cl)[C:19]2[CH:24]=[CH:23][NH:22][C:20]=2[N:21]=1>C1COCC1>[Cl:15][C:16]1[N:17]=[C:18]([O:11][C:7]2[C:6]([CH3:12])=[CH:5][C:4]([CH:1]3[CH2:3][CH2:2]3)=[CH:9][C:8]=2[CH3:10])[C:19]2[CH:24]=[CH:23][NH:22][C:20]=2[N:21]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 141168712,4-Dichloro-7H-pyrrolo[2,3-d]pyrimidineHCID 576935554-Cyclopropyl-2,6-dimethylphenol

생성물 1

HCID 576935762-chloro-4-(4-cyclopropyl-2,6-dimethylphenoxy)-7H-pyrrolo[2,3-d]pyrimidine수율 48%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of 4-cyclopropyl-2,6-dimethylphenol (259 mg, 1.60 mmol) in THF (3 mL) at 0° C. was added NaH (64 mg, 1.60 mmol). The reaction mixture was stirred at room temperature for 30 min and a solution of 2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine (100 mg, 0.53 mmol) in THF (2 mL) was added to the mixture. The mixture was heated at 80° C. for 16 h and cooled to room temperature. The reaction was poured into ice water and extracted with CHCl3 (3×20 mL). The combined organic solution was washed with H2O (20 mL) and brine (20 mL), dried with Na2SO4, and concentrated to dryness. Silica gel chromatography (Hexanes:EtOAc=75:25) yielded 79 mg (48%) of 2-chloro-4-(4-cyclopropyl-2,6-dimethylphenoxy)-7H-pyrrolo[2,3-d]pyrimidine as a tan solid.

후처리

  1. temperatureThe mixture was heated at 80° C. for 16 h
  2. temperaturecooled to room temperature
  3. extractionextracted with CHCl3 (3×20 mL)
  4. washThe combined organic solution was washed with H2O (20 mL) and brine (20 mL)
  5. dry with materialdried with Na2SO4
  6. concentrationconcentrated to dryness

출처 및 근거

ORD 기록
ord-eeb6f2a3eb9c4359b82738c83f3679cd
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08227601B2

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