Potassium Iodide → HCID 178456477, compound

HRID 1086834Notes

Reaction equation

HRID 1086834 reaction equation
[NH2:1][C:2]1[C:10]2[C:9](=[O:11])[N:8]([CH2:12][CH2:13][CH3:14])[C:7](=[O:15])[N:6]([CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[C:5]=2[NH:4][N:3]=1.[CH2:23](Cl)[C:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=O.C([O-])([O-])=O.[K+].[K+].[I-].[K+]>C(#N)C>[CH2:16]([N:6]1[C:5]2=[N:4][N:3]3[CH:23]=[C:24]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[NH:1][C:2]3=[C:10]2[C:9](=[O:11])[N:8]([CH2:12][CH2:13][CH3:14])[C:7]1=[O:15])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 107572-ChloroacetophenoneHCID 11430Potassium CarbonateHCID 178456480HCID 178456480, compound

Product 1

HCID 178456477HCID 178456477, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 3-amino-7-benzyl-5-propylpyrazolo [3,4-d]pyrimidine-4,6(5H,7H)-dione (2.0 g), phenacyl chloride (4.4 g), K2CO3 (2.5 g) and potassium iodide (1.4 g) in acetonitrile (150 ml) was stirred for 3 days at room temperature. Precipitating crystals were collected by filtration and washed with water. The filtrate was concentrated to give a syrup. The syrup was crystallized by the addition of isopropyl ether. The crystals were combined and dissolved in toluene (200 ml). To the solution was added p-toluenesulfonic acid (0.1 g), followed by heating for 3 hours under reflux. The reaction mixture was concentrated to dryness and then was added isopropyl ether to give crude crystals, followed by recrystallization from methanol to afford colorless crystals (1.1 g, 43%), m.p. 261°-262° C.

Workup

  1. customPrecipitating crystals
  2. filtrationwere collected by filtration
  3. washwashed with water
  4. concentrationThe filtrate was concentrated
  5. customto give a syrup
  6. customThe syrup was crystallized by the addition of isopropyl ether
  7. dissolutiondissolved in toluene (200 ml)
  8. additionTo the solution was added p-toluenesulfonic acid (0.1 g)
  9. temperatureby heating for 3 hours
  10. temperatureunder reflux
  11. concentrationThe reaction mixture was concentrated to dryness
  12. additionwas added isopropyl ether
  13. customto give crude crystals
  14. customfollowed by recrystallization from methanol

Sources & evidence

ORD record
ord-251be3906bb24e2e9f815ada409de657
Source dataset
uspto-grants-1991_07
Patent number
US05032594

Reaction notes

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