N-methyl-2-pyrrolidone → N-[4-(benzyloxy)-3-chlorophenyl]-5H-pyrrolo[3,2-d]pyrimidin-4-amine

HRID 1786925노트

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HRID 1786925 반응식
Cl[C:2]1[C:3]2[NH:10][CH:9]=[CH:8][C:4]=2[N:5]=[CH:6][N:7]=1.[CH2:11]([O:18][C:19]1[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][C:20]=1[Cl:26])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CN1CCCC1=O>CO>[CH2:11]([O:18][C:19]1[CH:25]=[CH:24][C:22]([NH:23][C:2]2[C:3]3[NH:10][CH:9]=[CH:8][C:4]=3[N:5]=[CH:6][N:7]=2)=[CH:21][C:20]=1[Cl:26])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

참가 물질

5

반응물 3

HCID 13387N-methyl-2-pyrrolidoneHCID 12682854-Benzyloxy-3-chloroanilineHCID 53706954-chloro-5H-pyrrolo[3,2-d]pyrimidine

생성물 1

HCID 57597271N-[4-(benzyloxy)-3-chlorophenyl]-5H-pyrrolo[3,2-d]pyrimidin-4-amine수율 49.5%

시약·촉매·용매 1

HCID 887Methanol용매

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온도
80 °C

실험 절차

A mixture of 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (200 mg), 4-(benzyloxy)-3-chloroaniline (365 mg) and 1-methyl-2-pyrrolidone (3 mL) was stirred at 80° C. for 4 hrs. Methanol and activated carbon were added to the reaction mixture and the mixture was stirred. The activated carbon was filtered off, aqueous sodium hydrogen carbonate solution was added and the mixture was extracted with ethyl acetate. The extract was washed with water and 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→15:75) and recrystallized from ethanol-ethyl acetate to give the title compound (226 mg) as a pale-brown powder.

후처리

  1. stirringthe mixture was stirred
  2. filtrationThe activated carbon was filtered off
  3. additionaqueous sodium hydrogen carbonate solution was added
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe extract was washed with water and 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→15:75)
  9. customrecrystallized from ethanol-ethyl acetate

출처 및 근거

ORD 기록
ord-69cd76e25f794ae5ae52dfdfac3d9ec8
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07507740B2

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