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

HRID 2234521
Notes
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Reaction equation

HRID 2234521 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium Carbonate2×HCID 5212662,4-Dichloro-5-nitropyrimidine2×HCID 68682361Ethyl1-[(cyclohexylamino)methyl]cyclopropane-1-carboxylate2×

Product 1

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

Reagents, catalysts & solvents 1

HCID 180
Acetone
Solvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-f668f30d58004eeba7c6955691de01dd
Source dataset
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07709471B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes