Citric Acid → 2-Butyl-3H-pyrrolo[3,2-d]pyrimidin-4(5H)-one

HRID 1487241Notes

Reaction equation

HRID 1487241 reaction equation
[OH-].[Na+].Cl.[C:4](=[NH:20])([NH:9][C:10]1[CH:14]=[CH:13][NH:12][C:11]=1[C:15](OCC)=[O:16])[CH2:5][CH2:6][CH2:7][CH3:8].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O.C(O)C>[CH2:5]([C:4]1[NH:20][C:15](=[O:16])[C:11]2[NH:12][CH:13]=[CH:14][C:10]=2[N:9]=1)[CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 178446840HCID 178446840, compound

Product 1

HCID 1370052332-Butyl-3H-pyrrolo[3,2-d]pyrimidin-4(5H)-oneYield 98.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of sodium hydroxide (1.44 g, 35.9 mmol) in water (7 mL) was added to a solution of ethyl 3-pentanimidamido-1H-pyrrole-2-carboxylate hydrochloride (2.46 g, 8.99 mmol) in ethanol (30 mL). The resultant mixture was heated at reflux for a total of 4 hours. The reaction mixture was cooled to room temperature and the pH adjusted to pH 6.5 with aqueous citric acid. The resultant mixture was extracted with ethyl acetate (2×50 mL). The combined organic phases were washed with saturated aqueous sodium chloride solution, dried (Na2SO4), filtered and evaporated to give the title compound as a pale brown solid (1.69 g).

Workup

  1. temperatureat reflux for a total of 4 hours
  2. extractionThe resultant mixture was extracted with ethyl acetate (2×50 mL)
  3. washThe combined organic phases were washed with saturated aqueous sodium chloride solution
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-ad9e653ce3454ba4b292c82afdf0a20b
Source dataset
uspto-grants-2016_08
Patent number
US09428512B2

Reaction notes

Loading…