Triethylamine → Ethyl 5-(1,3-dimethyl-2,4-dioxo-5-phenyl-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)pentanoate

HRID 2201271ノート

反応式

HRID 2201271 の反応式
[C:1]([C:9]1[C:10](=[O:20])[N:11]([CH3:19])[C:12](=[O:18])[N:13]([CH3:17])[C:14]=1[CH2:15]Br)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[NH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28].C(N(CC)CC)C>C(O)C>[CH3:17][N:13]1[C:14]2=[CH:15][N:22]([CH2:23][CH2:24][CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[C:9]2[C:10](=[O:20])[N:11]([CH3:19])[C:12]1=[O:18]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 9503195-Benzoyl-6-(bromomethyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione2 回HCID 16094861Ethyl 5-aminopentanoate hydrochloride

生成物 1

HCID 86723511Ethyl 5-(1,3-dimethyl-2,4-dioxo-5-phenyl-3,4-dihydro-1H-pyrrolo[3,4-d]pyrimidin-6(2H)-yl)pentanoate

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

5-Benzoyl-6-(bromomethyl)-1,3-dimethylpyrimidine-2,4(1H,3H)-dione (Intermediate C) (1.38 g, 4.09 mmol), ethyl 5-aminovalerate hydrochloride (1.109 g, 6.14 mmol) and triethylamine (1.711 mL, 12.28 mmol) were combined in ethanol (20 mL) and the mixture heated at reflux for 40 mins. The reaction mixture was cooled to room temperature and evaporated under vacuum. The residue was partitioned between water and DCM and the phases separated. The organic phase was passed through a hydrophobic frit and evaporated onto silica. The silica was deposited onto a 25 g silica cartridge and the system eluted with 20% EtOAc/hexane, 40% EtOAc/hexane, 60% EtOAc/hexane and 80% EtOAc/hexane. The product fractions were combined and concentrated under reduced pressure to afford the title compound;

後処理

  1. temperaturethe mixture heated
  2. temperatureat reflux for 40 mins
  3. customevaporated under vacuum
  4. customThe residue was partitioned between water and DCM
  5. customthe phases separated
  6. customevaporated onto silica
  7. washthe system eluted with 20% EtOAc/hexane, 40% EtOAc/hexane, 60% EtOAc/hexane and 80% EtOAc/hexane
  8. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-f0c5311b3eda4880b77a6a6a344db360
出典データセット
uspto-grants-2016_06
特許番号
US09359381B2

反応ノート

読み込み中…