Trifluoroacetic acid → 4-(4-(4-Cyclopropyl-2,6-dimethylphenoxy)-5H-pyrrolo[3,2-d]pyrimidin-2-ylamino)benzonitrile

HRID 1805871노트

반응식

HRID 1805871 반응식
Cl[C:2]1[N:3]=[C:4]([O:11][C:12]2[C:17]([CH3:18])=[CH:16][C:15]([CH:19]3[CH2:21][CH2:20]3)=[CH:14][C:13]=2[CH3:22])[C:5]2[NH:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[NH2:23][C:24]1[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[CH:26][CH:25]=1.C(O)(C(F)(F)F)=O>O>[CH:19]1([C:15]2[CH:16]=[C:17]([CH3:18])[C:12]([O:11][C:4]3[C:5]4[NH:10][CH:9]=[CH:8][C:6]=4[N:7]=[C:2]([NH:23][C:24]4[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[CH:26][CH:25]=4)[N:3]=3)=[C:13]([CH3:22])[CH:14]=2)[CH2:21][CH2:20]1

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acidHCID 133964-AminobenzonitrileHCID 576936052-chloro-4-(4-cyclopropyl-2,6-dimethylphenoxy)-5H-pyrrolo[3,2-d]pyrimidine

생성물 1

HCID 119624414-(4-(4-Cyclopropyl-2,6-dimethylphenoxy)-5H-pyrrolo[3,2-d]pyrimidin-2-ylamino)benzonitrile수율 45%

시약·촉매·용매 1

HCID 962Water용매

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온도
90 °C

실험 절차

In a sealed tube was placed 2-chloro-4-(4-cyclopropyl-2,6-dimethylphenoxy)-5H-pyrrolo[3,2-d]pyrimidine (20 mg, 0.064 mmol), 4-aminobenzonitrile (31 mg, 0.26 mmol), TFE (0.21 mL) and TFA (0.04 mL, 0.51 mmol). The reaction mixture was stirred at 90° C. for 16 h. Upon completion of the reaction, the resulting mixture was diluted with water and washed with EtOAc. The combined organic layers were washed with NaHCO3, brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by preparative TLC TLC, eluting with 5% Acetone/CH2Cl2 to give the product as a light yellow solid (10.5 mg, 45%).

후처리

  1. customIn a sealed tube was placed
  2. customUpon completion of the reaction
  3. washwashed with EtOAc
  4. washThe combined organic layers were washed with NaHCO3, brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by preparative TLC TLC
  9. washeluting with 5% Acetone/CH2Cl2

출처 및 근거

ORD 기록
ord-14df209e14484adb9a3824df91728f8b
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08354532B2

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