1,8-Diazabicyclo(5.4.0)undec-7-ene → 7-Allyl-8-(3,5-dimethylpiperazin-1-yl)-1,3-dimethyl-3,7-dihydropurine-2,6-dione

HRID 1792001ノート

反応式

HRID 1792001 の反応式
[CH2:1]([N:4]1[C:12]2[C:11](=[O:13])[N:10]([CH3:14])[C:9](=[O:15])[N:8]([CH3:16])[C:7]=2[N:6]=[C:5]1Cl)[CH:2]=[CH2:3].[CH3:18][C@H:19]1[CH2:24][NH:23][CH2:22][C@@H:21]([CH3:25])[NH:20]1.N12CCCN=C1CCCCC2>CN1CCCC1=O.C(OCC)(=O)C.O>[CH2:1]([N:4]1[C:12]2[C:11](=[O:13])[N:10]([CH3:14])[C:9](=[O:15])[N:8]([CH3:16])[C:7]=2[N:6]=[C:5]1[N:23]1[CH2:22][CH:21]([CH3:25])[NH:20][CH:19]([CH3:18])[CH2:24]1)[CH:2]=[CH2:3]

参加物

7

反応物 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 7386827-Allyl-8-chloro-1,3-dimethyl-3,7-dihydropurine-2,6-dioneHCID 6950261rel-(2R,6S)-2,6-dimethylpiperazine

生成物 1

HCID 220299077-Allyl-8-(3,5-dimethylpiperazin-1-yl)-1,3-dimethyl-3,7-dihydropurine-2,6-dione収率 42.5%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
150 °C

実験手順

A suspension of 7-allyl-8-chloro-1,3-dimethyl-3,7-dihydropurine-2,6-dione (200 mg), cis-2,6-dimethylpiperazine (107 mg), and 1,8-diazabicyclo[5.4.0]undec-7-ene (128 μl) in 1-methyl-2-pyrrolidone (2 ml) was stirred at 150° C. for 50 minutes. The reaction mixture was diluted with ethyl acetate and water, and extracted with ethyl acetate. The aqueous layer was extracted with chloroform, and the combined organic layer was washed with water and dried over magnesium sulfate. The solvent was removed by distillation at reduced pressure to give brown oil. The oil was purified by silica gel column chromatography, and 111 mg of the title compound was obtained from a fraction eluted with methanol-ethyl acetate (1:10).

後処理

  1. extractionextracted with ethyl acetate
  2. extractionThe aqueous layer was extracted with chloroform
  3. washthe combined organic layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed by distillation at reduced pressure
  6. customto give brown oil
  7. customThe oil was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-fa8fc4c9e9274884abd572fa6fada0e9
出典データセット
uspto-grants-2006_07
特許番号
US07074798B2

反応ノート

読み込み中…