Phosphorus sulfide (P2S5) → HCID 178527902, compound

HRID 1692730Notes

Reaction equation

HRID 1692730 reaction equation
P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:2].[Cl:15][C:16]1[CH:17]=[C:18]([CH:35]=[CH:36][CH:37]=1)[CH2:19][C:20]1[NH:21][C:22](=O)[C:23]2[CH:28]=[N:27][N:26]([CH:29]3[CH2:33][CH2:32][CH2:31][CH2:30]3)[C:24]=2[N:25]=1.C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[Cl:15][C:16]1[CH:17]=[C:18]([CH:35]=[CH:36][CH:37]=1)[CH2:19][C:20]1[NH:21][C:22](=[S:2])[C:23]2[CH:28]=[N:27][N:26]([CH:29]3[CH2:33][CH2:32][CH2:31][CH2:30]3)[C:24]=2[N:25]=1

Participants

5

Reactant 3

HCID 14817Phosphorus sulfide (P2S5)HCID 516892Sodium BicarbonateHCID 1354823306-(3-Chlorobenzyl)-1-cyclopentyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one

Product 1

HCID 178527902HCID 178527902, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

50 mg (0.23 mmol, 1.5 equiv.) of diphosphorus pentasulfide are added to a solution of 50 mg (0.15 mmol) of 6-(3-chlorobenzyl)-1-cyclopentyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one (Example 1) in 1 ml of pyridine at room temperature, and the mixture is then stirred under reflux overnight. After cooling, the reaction solution is mixed with 10 ml of ice-cold 2.5% strength sodium bicarbonate solution and extracted three times with ethyl acetate. The combined organic phases are washed with saturated brine, dried over sodium sulfate and concentrated in vacuo. The crude product is purified by preparative HPLC.

Workup

  1. temperatureunder reflux overnight
  2. temperatureAfter cooling
  3. extractionextracted three times with ethyl acetate
  4. washThe combined organic phases are washed with saturated brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe crude product is purified by preparative HPLC

Sources & evidence

ORD record
ord-7ce45d25c56645c3bac28e70c48862da
Source dataset
uspto-grants-2012_04
Patent number
US08158633B2

Reaction notes

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