Formamidine acetate → ethyl 4-(4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-6-yl)benzoate

HRID 1926025Notes

Reaction equation

HRID 1926025 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:9][CH:8]=2)[NH:4][C:3]=1[C:18]([O:20]CC)=O.C(O)(=O)C.[CH:27](N)=[NH:28]>C(O)C>[O:20]=[C:18]1[NH:28][CH:27]=[N:1][C:2]2[CH:6]=[C:5]([C:7]3[CH:8]=[CH:9][C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:11][CH:12]=3)[NH:4][C:3]1=2

Participants

4

Reactant 2

HCID 160693Formamidine acetateHCID 67520621ethyl 3-amino-5-[4-(ethoxycarbonyl)phenyl]-1H-pyrrole-2-carboxylate

Product 1

HCID 136354574ethyl 4-(4-oxo-4,5-dihydro-3H-pyrrolo[3,2-d]pyrimidin-6-yl)benzoateYield 94.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 3-amino-5-[4-(ethoxycarbonyl)phenyl]-1H-pyrrole-2-carboxylate (3.36 g), formamidine acetate (1.74 g) and ethanol (60 mL) was heated under reflux for 15 hrs. After cooling to room temperature, the precipitated solid was collected by filtration, washed with ethanol, and dried under reduced pressure at 60° C. to give the title compound (2.97 g).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 15 hrs
  3. filtrationthe precipitated solid was collected by filtration
  4. washwashed with ethanol
  5. customdried under reduced pressure at 60° C.

Sources & evidence

ORD record
ord-5fe21477c3044b9aab2c54008c92a50b
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

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