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Potassium Carbonate → Ethyl1-[[(2-chloro-5-nitro-pyrimidin-4-yl)-cyclohexyl-amino]methyl]cyclopropane-1-carboxylate

HRID 2234521
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HRID 2234521 반응식
[CH2:1]([O:3][C:4]([C:6]1([CH2:9][NH:10][CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[Cl:23][C:24]1[N:29]=[C:28](Cl)[C:27]([N+:31]([O-:33])=[O:32])=[CH:26][N:25]=1>CC(C)=O>[CH2:1]([O:3][C:4]([C:6]1([CH2:9][N:10]([C:26]2[C:27]([N+:31]([O-:33])=[O:32])=[CH:28][N:29]=[C:24]([Cl:23])[N:25]=2)[CH:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH2:7][CH2:8]1)=[O:5])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 11430Potassium Carbonate2회HCID 5212662,4-Dichloro-5-nitropyrimidine2회HCID 68682361Ethyl1-[(cyclohexylamino)methyl]cyclopropane-1-carboxylate2회

생성물 1

HCID 86617593Ethyl1-[[(2-chloro-5-nitro-pyrimidin-4-yl)-cyclohexyl-amino]methyl]cyclopropane-1-carboxylate수율 92.2%

시약·촉매·용매 1

HCID 180
Acetone
용매

실험 절차

To a solution of ethyl1-[(cyclohexylamino)methyl]cyclopropane-1-carboxylate (Intermediate 273; 7.175 g, 34 mmol) in acetone (200 mL) was added potassium carbonate 7.05 g, 51 mmol) followed by 2,4-dichloro-5-nitropyrimidine (Aldrich; 9.235 g, 47.6 mmol). The reaction mixture was stirred at room temperature for 5 hours. A further addition of 2,4-dichloro-5-nitropyrimidine (4.62 g, 23.8 mmol) and potassium carbonate (3.5 g, 25.5 mmol) was made and the reaction stirred overnight at room temperature. The reaction mixture was then concentrated in vacuo and partitioned between EtOAc and water. The EtOAc layer was separated, dried over sodium sulphate and purified on a silica column eluting with EtOAc/isohexane 10:90, to yield the title compound as a yellow oil (12 g, 92%).

후처리

  1. stirringthe reaction stirred overnight at room temperature
  2. concentrationThe reaction mixture was then concentrated in vacuo
  3. custompartitioned between EtOAc and water
  4. customThe EtOAc layer was separated
  5. dry with materialdried over sodium sulphate
  6. custompurified on a silica column
  7. washeluting with EtOAc/isohexane 10:90

출처 및 근거

ORD 기록
ord-f668f30d58004eeba7c6955691de01dd
출처 데이터셋
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07709471B2

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