Methyl 2-pyridylacetate → HCID 178437870, compound

HRID 2257023Notes

Reaction equation

HRID 2257023 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.[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=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:19]4[CH:20]=[CH:21][CH:22]=[CH:23][N:18]=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 74264Methyl 2-pyridylacetateHCID 5360545SodiumHCID 224493525-amino-1-cyclopentyl-3-ethyl-1H-pyrazole-4-carboxamide

Product 1

HCID 178437870HCID 178437870, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium metal (310 mg) was dissolved in ethanol (75 ml) and then 1-cyclopentyl-3-ethyl-5-amino-1H-pyrazole-4-carboxamide (1.1 g, 5 mmol) and methyl 2-pyridinylacetate (1.52 g, 10 mmol) were added. The reaction mixture was heated at reflux for 28 hours, the solvent was removed in vacuo and the residue was dissolved in water (50 ml) and acidified with acetic acid. The mixture was extracted with CHCl3 (100 ml), the solvent was removed and the oily residue was crystallized from cyclohexane to afford 0.85 g of crude product. The product was purified by column chromatography on silica gel eluting with ether, followed by recrystallization from cyclohexane, to afford 1-cyclopentyl-3-ethyl-6-(2-pyridinylmethyl)pyrazolo[3,4-d]pyrimidin-4-one, as yellow crystals, m.p. 120°-122° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 28 hours
  3. customthe solvent was removed in vacuo
  4. dissolutionthe residue was dissolved in water (50 ml)
  5. extractionThe mixture was extracted with CHCl3 (100 ml)
  6. customthe solvent was removed
  7. customthe oily residue was crystallized from cyclohexane
  8. customto afford 0.85 g of crude product
  9. customThe product was purified by column chromatography on silica gel eluting with ether
  10. customfollowed by recrystallization from cyclohexane

Sources & evidence

ORD record
ord-0e5c39346fe246ae8c3a7a9a41a5131f
Source dataset
uspto-grants-1997_08
Patent number
US05656629

Reaction notes

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