Water → Pyrazolo[3,4-d]pyrimidin-4-one

HRID 619147Notes

Reaction equation

HRID 619147 reaction equation
[Na].C1([N:7]2[C:11]([NH2:12])=[C:10]([C:13]([NH2:15])=[O:14])[C:9](CC)=[N:8]2)CCCC1.[CH2:18](OC1C=CC=CC=1C(OCC)=O)C=C.O>C(O)C.CCOCC>[N:7]1[C:11]2=[N:12][CH:18]=[N:15][C:13](=[O:14])[C:10]2=[CH:9][N:8]=1

Participants

7

Reactant 4

HCID 962WaterHCID 5360545SodiumHCID 10398065Benzoic acid, 2-(2-propenyloxy)-, ethyl esterHCID 224493525-amino-1-cyclopentyl-3-ethyl-1H-pyrazole-4-carboxamide

Product 1

HCID 22252149Pyrazolo[3,4-d]pyrimidin-4-one

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

Sodium spheres (207 mg) was dissolved in ethanol (15 ml) and 1-cyclopentyl-3-ethyl-5-amino-1H-pyrazole-4-carboxamide (1 g, 45 mmol) was added, followed by ethyl 2-(2-propenyloxy)benzoate (1.85 g, 9 mmol). The reaction mixture was refluxed overnight, cooled, the ethanol was stripped and water was added. The pH was adjusted to about 7 and a solid was isolated by filtration. The solid was taken up in ether, washed with dilute HCl, dried over MgSO4, filtered and the solvent was removed and the solid residue was recrystallized from ether to afford 0.56 g of 1-cyclopentyl-3-ethyl-6-[2-(CH2 =CH--CH2O)phenyl]pyrazolo[3,4-d]pyrimidin-4-one, m.p. 119-120° C.

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. temperaturecooled
  3. customa solid was isolated by filtration
  4. washwashed with dilute HCl
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customthe solvent was removed
  8. customthe solid residue was recrystallized from ether

Sources & evidence

ORD record
ord-76dfea2568dd44bc962b043c40ce711b
Source dataset
uspto-grants-1999_09
Patent number
US05958929

Reaction notes

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