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

HRID 1786938Notes

Reaction equation

HRID 1786938 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-23398c4f680f4fd6a53b3b6ec365b20c
Source dataset
uspto-grants-2009_03
Patent number
US07507740B2

Reaction notes

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