4-chloro-5H-pyrrolo[3,2-d]pyrimidine → [2-(benzyloxy)-5-(5H-pyrrolo[3,2-d]pyrimidin-4-ylamino)phenyl]methanol

HRID 1926010노트

반응식

HRID 1926010 반응식
Cl[C:2]1[C:3]2[NH:10][CH:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[NH2:11][C:12]1[CH:13]=[CH:14][C:15]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:16]([CH2:18][OH:19])[CH:17]=1>CN(C)C=O>[CH2:21]([O:20][C:15]1[CH:14]=[CH:13][C:12]([NH:11][C:2]2[C:3]3[NH:10][CH:9]=[CH:8][C:4]=3[N:5]=[CH:6][N:7]=2)=[CH:17][C:16]=1[CH2:18][OH:19])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

참가 물질

4

반응물 2

HCID 53706954-chloro-5H-pyrrolo[3,2-d]pyrimidineHCID 219043564-Benzyloxy-3-hydroxymethylaniline

생성물 1

HCID 57597321[2-(benzyloxy)-5-(5H-pyrrolo[3,2-d]pyrimidin-4-ylamino)phenyl]methanol수율 40.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

A mixture of 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (307 mg), [5-amino-2-(benzyloxy)phenyl]methanol (459 mg) and N,N-dimethylformamide (10 mL) was stirred at 80° C. for 4 hrs. The reaction mixture was concentrated under reduced pressure, aqueous sodium hydrogen carbonate solution was added and the mixture was extracted with ethyl acetate containing tetrahydrofuran. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (eluent, methanol:ethyl acetate=0:100→30:70). Ethanol and ethyl acetate were added and the precipitate was collected by filtration to give the title compound (279 mg) as a brown powder.

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure, aqueous sodium hydrogen carbonate solution
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. additioncontaining tetrahydrofuran
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe obtained residue was purified by silica gel column chromatography (eluent, methanol:ethyl acetate=0:100→30:70)
  9. additionEthanol and ethyl acetate were added
  10. filtrationthe precipitate was collected by filtration

출처 및 근거

ORD 기록
ord-b66d091d05e5401fb2b9115ccc1c792b
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08178543B2

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