Methyl 1-methylpyrrol-2-acetate → HCID 178437873, compound

HRID 1600810Notes

Reaction equation

HRID 1600810 reaction equation
[Na].[CH:2]1([N:7]2[C:11]([NH2:12])=[C:10]([C:13]([NH2:15])=[O:14])[C:9]([CH2:16][CH3:17])=[N:8]2)[CH2:6][CH2:5][CH2:4][CH2:3]1.[CH3:18][N:19]1[CH:23]=[CH:22][CH:21]=[C:20]1[CH2:24][C:25](OC)=O>C(O)C>[CH:2]1([N:7]2[C:11]3=[N:12][C:25]([CH2:24][C:20]4[N:19]([CH3:18])[CH:23]=[CH:22][CH:21]=4)=[N:15][C:13](=[O:14])[C:10]3=[C:9]([CH2:16][CH3:17])[NH:8]2)[CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 103992Methyl 1-methylpyrrol-2-acetateHCID 5360545SodiumHCID 224493525-amino-1-cyclopentyl-3-ethyl-1H-pyrazole-4-carboxamide

Product 1

HCID 178437873HCID 178437873, compoundYield 36.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Sodium spheres (1.0 g, 43.5 mmol) were dissolved in ethanol (50 mL) at reflux and then 1-cyclopentyl-3-ethyl-5-amino-1H-pyrazole-4-carboxamide (2.2 g, 10 mmol), followed by methyl 1-methylpyrrole-2-acetate (3.06 g, 20 mmol) in ethanol (30 mL) were added. The reaction mixture was refluxed under argon overnight, cooled to room temperature and evaporated to dryness. The residue was dissolved in water, the solution was cooled and the resulting solid was collected by filtration to afford recovered starting material. The filtrate was chilled, a solid formed which was collected by filtration, slurried with water and acidified with 2N HCl. The mixture was cooled and the product was collected by filtration and dried at 110° C. in vacuo to afford 1.2 g of 1-cyclopentyl-3-ethyl-6-(1-methyl-2-pyrrolylmethyl)pyrazolo[3,4-d]pyrimidin-4-one, m.p. 214.5-216.5° C. Additional product (0.6 g) was also obtained by acidifying the filtrate with acetic acid, collecting the product by filtration and recrystallizing it from ethyl acetate.

Workup

  1. temperatureat reflux
  2. additionwere added
  3. temperatureThe reaction mixture was refluxed under argon overnight
  4. customevaporated to dryness
  5. dissolutionThe residue was dissolved in water
  6. temperaturethe solution was cooled
  7. filtrationthe resulting solid was collected by filtration
  8. customto afford
  9. customrecovered
  10. temperatureThe filtrate was chilled
  11. customa solid formed which
  12. filtrationwas collected by filtration
  13. temperatureThe mixture was cooled
  14. filtrationthe product was collected by filtration
  15. customdried at 110° C. in vacuo

Sources & evidence

ORD record
ord-e7fedba4dcd144d9acdedc90dac68ff3
Source dataset
uspto-grants-1999_11
Patent number
US05977118

Reaction notes

Loading…