Acetic Acid → Ethyl imidazo(1,2-c)pyrimidine-7-carboxylate

HRID 25166

Reaction equation

HRID 25166 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]=O.[N+:8]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])#[C-:9].C1CCN2C(=NCCC2)CC1.CC(O)=O>O1CCOCC1>[N:3]1[CH:4]=[CH:5][N:1]2[C:2]=1[CH:6]=[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:8]=[CH:9]2

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 249551H-imidazole-2-carbaldehydeHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 533707Ethyl isocyanoacetate

Product 1

HCID 22566015Ethyl imidazo(1,2-c)pyrimidine-7-carboxylate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a suspension of imidazole-2-carboxaldehyde (2.3 g, 23.4 mmol) in 50 mL dioxane is added to ethyl isocyanoacetate (2.9 g, 25.8 mmol) and DBU (3.9 g, 25.8 mmol). After stirring at RT for 5 days, the reaction is neutralized with 10% AcOH. The solvent is removed in vacuo. The residue is taken up in EtOAc/H2O, the aqueous layer is extracted with CHCl3, dried (MgSO4), filtered and concentrated. The residue is purified by chromatography (Biotage 40M, eluting with 5% MeOH/EtOAc). Ethyl imidazo[1,2-c]pyrimidine-7-carboxylate is obtained (1.4 g, 32%) as an off-white solid. 1H NMR (400 MHz, CDCl3) δ9.14, 8.43, 7.88, 7.81, 4.54-4.48, 1.49-1.44.

Workup

  1. customThe solvent is removed in vacuo
  2. extractionthe aqueous layer is extracted with CHCl3
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is purified by chromatography (Biotage 40M, eluting with 5% MeOH/EtOAc)

Sources & evidence

ORD record
ord-75566e8a19114934948489b12d480eb1
Source dataset
uspto-grants-2005_02
Patent number
US06858613B2

Linked notes

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