Formamidine acetate → 6-(furan-2-yl)-5H-pyrrolo[3,2-d]pyrimidin-4-ol

HRID 1926018Notes

Reaction equation

HRID 1926018 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([C:7]2[O:8][CH:9]=[CH:10][CH:11]=2)[NH:4][C:3]=1[C:12]([O:14]CC)=O.C(O)(=O)C.[CH:21](N)=[NH:22]>C(O)C>[O:8]1[CH:9]=[CH:10][CH:11]=[C:7]1[C:5]1[NH:4][C:3]2[C:12](=[O:14])[NH:22][CH:21]=[N:1][C:2]=2[CH:6]=1

Participants

4

Reactant 2

HCID 160693Formamidine acetateHCID 10751393ethyl 3-amino-5-(furan-2-yl)-1H-pyrrole-2-carboxylate

Product 1

HCID 1357417756-(furan-2-yl)-5H-pyrrolo[3,2-d]pyrimidin-4-olYield 95.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 3-amino-5-(2-furyl)-1H-pyrrole-2-carboxylate (2.58 g) in ethanol (35 mL) was added formamidine acetate (1.83 g), and the mixture was heated under reflux for 18 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 (2.26 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 18 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-0892badb54c14fb6b553e8368b245712
Source dataset
uspto-grants-2012_05
Patent number
US08178543B2

Reaction notes

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