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

HRID 2234477Notes

Reaction equation

HRID 2234477 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([CH2:9][NH:10][CH:11]([CH3:13])[CH3:12])[CH2:8][CH2:7]1)=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[Cl:20][C:21]1[N:26]=[C:25](Cl)[C:24]([N+:28]([O-:30])=[O:29])=[CH:23][N:22]=1>CC(C)=O>[CH2:1]([O:3][C:4]([C:6]1([CH2:9][N:10]([C:23]2[C:24]([N+:28]([O-:30])=[O:29])=[CH:25][N:26]=[C:21]([Cl:20])[N:22]=2)[CH:11]([CH3:12])[CH3:13])[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5212662,4-Dichloro-5-nitropyrimidineHCID 68684554Ethyl1-[(propan-2-ylamino)methyl]cyclopropane-1-carboxylate2×

Product 1

HCID 86617588Ethyl1-[[(2-chloro-5-nitro-pyrimidin-4-yl)-propan-2-yl-amino]methyl]cyclopropane-1-carboxylate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of ethyl1-[(propan-2-ylamino)methyl]cyclopropane-1-carboxylate (Intermediate 211; 9.55 g, 50 mmol) in acetone (300 mL) was added potassium carbonate (7.05 g, 51 mmol) followed by 2,4-dichloro-5-nitropyrimidine (Aldrich; 10.675 g, 55 mmol). The mixture was stirred overnight at room temperature, concentrated in vacuo and partitioned between EtOAc and water. The EtOAc layer was separated, dried over sodium sulfate, then purified by column chromatography (EtOAc/isohexane 10:90), to yield the title compound as a yellow oil. (11 g, 64%)

Workup

  1. concentrationconcentrated in vacuo
  2. custompartitioned between EtOAc and water
  3. customThe EtOAc layer was separated
  4. dry with materialdried over sodium sulfate
  5. custompurified by column chromatography (EtOAc/isohexane 10:90)

Sources & evidence

ORD record
ord-cca8b1dc53e84a0fb382f27467e08b57
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

Loading…