Aluminum(III) Chloride → 4-[4-(2,4,6-trimethyl-phenoxy)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino]-benzonitrile

HRID 1805834노트

반응식

HRID 1805834 반응식
C([N:8]1[C:12]2[N:13]=[C:14]([NH:27][C:28]3[CH:35]=[CH:34][C:31]([C:32]#[N:33])=[CH:30][CH:29]=3)[N:15]=[C:16]([O:17][C:18]3[C:23]([CH3:24])=[CH:22][C:21]([CH3:25])=[CH:20][C:19]=3[CH3:26])[C:11]=2[CH:10]=[CH:9]1)C1C=CC=CC=1.[Cl-].[Al+3].[Cl-].[Cl-]>ClC1C=CC=CC=1Cl>[CH3:26][C:19]1[CH:20]=[C:21]([CH3:25])[CH:22]=[C:23]([CH3:24])[C:18]=1[O:17][C:16]1[C:11]2[CH:10]=[CH:9][NH:8][C:12]=2[N:13]=[C:14]([NH:27][C:28]2[CH:35]=[CH:34][C:31]([C:32]#[N:33])=[CH:30][CH:29]=2)[N:15]=1

참가 물질

4

반응물 2

HCID 6451240Aluminum(III) ChlorideHCID 576935804-[7-benzyl-4-(2,4,6-trimethyl-phenoxy)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino]-benzonitrile

생성물 1

HCID 576936304-[4-(2,4,6-trimethyl-phenoxy)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino]-benzonitrile수율 49%

시약·촉매·용매 1

HCID 72391,2-Dichlorobenzene용매

반응 조건

온도
160 °C

실험 절차

To a solution of 4-[7-benzyl-4-(2,4,6-trimethyl-phenoxy)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino]-benzonitrile (38 mg, 0.083 mmol) in 1,2-dichlorobenzene (1 mL) was added aluminum chloride (55 mg, 0.42 mmol). The reaction mixture was stirred at 160° C. for 4 h and cooled to room temperature. The mixture was poured into ice water and extracted with CH2Cl2 (2×10 mL). The combined organic solution was washed with brine (10 mL), dried with Na2SO4, and concentrated to dryness. Silica gel chromatography (Hexanes:EtOAc=50:50) yielded 15 mg (49%) of 4-[4-(2,4,6-trimethyl-phenoxy)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino]-benzonitrile as a tan solid.

후처리

  1. temperaturecooled to room temperature
  2. extractionextracted with CH2Cl2 (2×10 mL)
  3. washThe combined organic solution was washed with brine (10 mL)
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated to dryness

출처 및 근거

ORD 기록
ord-d39ded26d96346a681333db7fe90f1a2
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08354532B2

반응 노트

불러오는 중…