Phosphorus sulfide (P2S5) → HCID 178446234, compound

HRID 400492Notes

Reaction equation

HRID 400492 reaction equation
P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:2].[CH:15]1([CH2:21][C:22]2[NH:23][C:24](=O)[C:25]3[CH:30]=[N:29][N:28]([CH:31]([CH2:34][CH3:35])[CH2:32][CH3:33])[C:26]=3[N:27]=2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[CH:15]1([CH2:21][C:22]2[NH:23][C:24](=[S:2])[C:25]3[CH:30]=[N:29][N:28]([CH:31]([CH2:34][CH3:35])[CH2:32][CH3:33])[C:26]=3[N:27]=2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 14817Phosphorus sulfide (P2S5)HCID 516892Sodium BicarbonateHCID 1354229306-(Cyclohexylmethyl)-1-(1-ethylpropyl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one

Product 1

HCID 178446234HCID 178446234, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

74 mg (0.33 mmol, 2 equiv.) of diphosphorus pentasulfide are added to a solution of 50 mg (0.17 mmol) of 6-(cyclohexylmethyl)-1-(1-ethylpropyl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one (Example 3) 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 20 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-df15d43ceed34b99ae73a11cd31ecb3e
Source dataset
uspto-grants-2014_06
Patent number
US08741907B2

Reaction notes

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