Methanesulfonic Acid → HCID 178437841, compound

HRID 487248

Reaction equation

HRID 487248 reaction equation
[CH:1]1([N:6]2[C:10]([NH2:11])=[C:9]([C:12]([NH2:14])=[O:13])[C:8]([CH2:15][CH3:16])=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:17][C:18]1[N:23]=[C:22]([CH:24]=O)[CH:21]=[CH:20][CH:19]=1.CS(O)(=O)=O>>[CH:1]1([N:6]2[C:10]3=[N:11][C:24]([C:22]4[CH:21]=[CH:20][CH:19]=[C:18]([CH3:17])[N:23]=4)=[N:14][C:12](=[O:13])[C:9]3=[C:8]([CH2:15][CH3:16])[NH:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 3

HCID 6395Methanesulfonic AcidHCID 707376-Methyl-2-pyridinecarboxaldehydeHCID 224493525-amino-1-cyclopentyl-3-ethyl-1H-pyrazole-4-carboxamide

Product 1

HCID 178437841HCID 178437841, compoundYield 53.3%

Procedure

1-Cyclopentyl-3-ethyl-5-amino-1H-pyrazole-4-carboxamide (2.0 g, 9.0 mmol), 6-methyl-2-pyridinecarboxaldehyde (2.2 g, 18.0 mmol), methanesulfonic acid (0.5 ml) and xylenes (80 ml) were combined and heated to reflux for 24 hours. The solvents were removed in vacuo, ethanol was added and the solvents were removed in vacuo. The residue was partitioned between 10% K2CO3 and chloroform, the organic layer was separated and the aqueous layer was extracted with chloroform (3×200 ml). The combined organic layers were concentrated in vacuo, redissolved in dichloromethane and combined with silica gel (40 g). The slurry was air dried for 3 hours, and placed on a silica gel column (150 g). Elution with ether and concentration of the solvent in vacuo and drying the residue at 40° C. in high vacuum for 6 hours afforded 1.55 g (53%) of 1-cyclopentyl-3-ethyl-6-(6-methyl-2-pyridyl)-pyrazolo[3,4-d]pyrimidin-4-one.

Workup

  1. temperatureheated
  2. temperatureto reflux for 24 hours
  3. customThe solvents were removed in vacuo, ethanol
  4. additionwas added
  5. customthe solvents were removed in vacuo
  6. customThe residue was partitioned between 10% K2CO3 and chloroform
  7. customthe organic layer was separated
  8. extractionthe aqueous layer was extracted with chloroform (3×200 ml)
  9. concentrationThe combined organic layers were concentrated in vacuo
  10. dissolutionredissolved in dichloromethane
  11. customdried for 3 hours
  12. washElution with ether and concentration of the solvent in vacuo
  13. customdrying the residue at 40° C. in high vacuum for 6 hours

Sources & evidence

ORD record
ord-36920c4b9c2e4c60843c0856108c7a55
Source dataset
uspto-grants-1994_03
Patent number
US05294612

Linked notes

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