Triethylamine → tert-butyl 5-((2,5-dichloropyrimidin-4-yl)amino)hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate

HRID 1056633ノート

反応式

HRID 1056633 の反応式
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([Cl:9])=[CH:4][N:3]=1.[NH2:10][CH:11]1[CH2:25][CH:14]2[CH2:15][N:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][CH:13]2[CH2:12]1.CCN(CC)CC>CCO>[Cl:1][C:2]1[N:7]=[C:6]([NH:10][CH:11]2[CH2:25][CH:14]3[CH2:15][N:16]([C:18]([O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:19])[CH2:17][CH:13]3[CH2:12]2)[C:5]([Cl:9])=[CH:4][N:3]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 2372592,4,5-TrichloropyrimidineHCID 59011518Tert-butyl 5-amino-octahydrocyclopenta[c]pyrrole-2-carboxylate

生成物 1

HCID 118389983tert-butyl 5-((2,5-dichloropyrimidin-4-yl)amino)hexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate収率 100%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of 2,4,5-trichloropyrimidine (1.46 g, 7.96 mmol) and tert-butyl 5-aminohexahydrocyclopenta[c]pyrrole-2(1H)-carboxylate (3.11 g, 13.74 mmol) in EtOH (60 mL) was added Et3N (2.21 g, 21.84 mmol) and the reaction mixture was stirred at rt overnight and then concentrated in vacuo. The residue was dissolved in a mixture of EtOAc (50 mL) and water (50 mL), and extracted with EtOAc (150 mL×3). The combined organic phases were washed with brine (150 mL), dried over anhydrous Na2SO4, then concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=1/5) to give the title compound as a pale yellow solid (2.97 g, 100%).

後処理

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in a mixture of EtOAc (50 mL) and water (50 mL)
  3. extractionextracted with EtOAc (150 mL×3)
  4. washThe combined organic phases were washed with brine (150 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography (EtOAc/PE (v/v)=1/5)

出典と根拠

ORDレコード
ord-7db4b538fc8d4575b2285d6b34ee9733
出典データセット
uspto-grants-2016_07
特許番号
US09399637B2

反応ノート

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