1,2-Dichloroethane → Ethyl 1-[(pyrimidin-5-ylcarbonyl)amino]-cyclopropanecarboxylate

HRID 2055574Notes

Reaction equation

HRID 2055574 reaction equation
C(N(CC)CC)C.[Cl-].[CH2:9]([O:11][C:12]([C:14]1([NH3+:17])[CH2:16][CH2:15]1)=[O:13])[CH3:10].[N:18]1[CH:23]=[C:22]([C:24](O)=[O:25])[CH:21]=[N:20][CH:19]=1.C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1>C(Cl)Cl>[N:18]1[CH:23]=[C:22]([C:24]([NH:17][C:14]2([C:12]([O:11][CH2:9][CH3:10])=[O:13])[CH2:16][CH2:15]2)=[O:25])[CH:21]=[N:20][CH:19]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 78346Pyrimidine-5-carboxylic acidHCID 181649HOAtHCID 91658617(1-Ethoxycarbonylcyclopropyl)azanium chloride

Product 1

HCID 67444517Ethyl 1-[(pyrimidin-5-ylcarbonyl)amino]-cyclopropanecarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (7.026 g, 69.44 mmol) was added to a suspension of 1-(ethoxycarbonyl)cyclopropanaminium chloride (11.50 g, 69.44 mmol), pyrimidine-5-carboxylic acid (8.617 g, 69.44 mmol), EDC (13.312 g, 69.44 mmol), and HOAT (0.945 g, 69.44 mmol) in CH2Cl2 (125 mL) and allowed to stir for 16 hours. The reaction was adsorbed onto silica and purified by silica gel chromatography and eluted with ethyl acetate to yield ethyl 1-[(pyrimidin-5-ylcarbonyl)amino]-cyclopropanecarboxylate as a white solid. Low resolution mass spectrometry: (M+H+)=236.2.

Workup

  1. custompurified by silica gel chromatography
  2. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-cad218f086cc47138a4301be644bec99
Source dataset
uspto-grants-2008_02
Patent number
US07332499B2

Reaction notes

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