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

HRID 1926012

反応式

HRID 1926012 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-c3bc6c71beef42a0b95fbac1f05738e5
出典データセット
uspto-grants-2012_05
特許番号
US08178543B2

関連ノート

読み込み中…