Aniline → HCID 178437891, compound

HRID 1600825Notes

Reaction equation

HRID 1600825 reaction equation
[CH:1]1([N:6]2[C:10]3=[N:11][C:12](S(C)(=O)=O)=[N:13][C:14](=[O:15])[C:9]3=[C:8]([CH2:20][CH3:21])[NH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C([O-])(O)=O.[Na+]>CCOCC>[CH:1]1([N:6]2[C:10]3=[N:11][C:12]([NH:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[N:13][C:14](=[O:15])[C:9]3=[C:8]([CH2:20][CH3:21])[NH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6115AnilineHCID 516892Sodium BicarbonateHCID 178437894HCID 178437894, compound

Product 1

HCID 178437891HCID 178437891, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
185 °C

Procedure

A mixture of 1-cyclopentyl-3-ethyl-6-(methylsulfonyl) pyrazolo[3,4-d]pyrimidin-4-one (2.3 g, 7.4 mmol) and aniline (1.2 g, 13 mmol) was heated at 180-190° C. for 3 hours. The reaction mixture was cooled to room temperature and allowed to stand at room temperature overnight. Ether was added to the reaction mixture and the product was collected by filtration, washed with ether and dried at 80-85° C. in a vacuum oven to afford crude product. The crude product was treated with saturated NaHCO3 (25 mL) and the insoluble material was collected by filtration, dissolved in hot isopropanol, treated with charcoal and concentrated in vacuo. The residue was crystallized from ether and dried at 80-85° C. in a vacuum oven to afford 0.58 g (25%) of 1-cyclopentyl-3-ethyl-6-(phenylamino)pyrazolo[3,4-d]pyrimidin-4-one.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationthe product was collected by filtration
  3. washwashed with ether
  4. customdried at 80-85° C. in a vacuum oven
  5. customto afford crude product
  6. filtrationthe insoluble material was collected by filtration
  7. dissolutiondissolved in hot isopropanol
  8. additiontreated with charcoal
  9. concentrationconcentrated in vacuo
  10. customThe residue was crystallized from ether
  11. customdried at 80-85° C. in a vacuum oven

Sources & evidence

ORD record
ord-56c8fa8193e947ada57a59538af1ecd2
Source dataset
uspto-grants-1999_11
Patent number
US05977118

Reaction notes

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