Hydrochloric Acid → 7-Benzyl-3-pentyl-6-thioxo-1,3,6,7-tetrahydro-2H-purin-2-one

HRID 2374301Notes

Reaction equation

HRID 2374301 reaction equation
[CH2:1]([N:8]1[C:16]2[C:15](=O)[NH:14][C:13](=[O:18])[N:12]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:11]=2[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:25].[OH-].[Na+].Cl>O1CCOCC1.O>[CH2:1]([N:8]1[C:16]2[C:15](=[S:25])[NH:14][C:13](=[O:18])[N:12]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:11]=2[N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 14817Phosphorus sulfide (P2S5)HCID 598538537-Benzyl-3-pentyl-3,7-dihydro-1H-purine-2,6-dione

Product 1

HCID 598538277-Benzyl-3-pentyl-6-thioxo-1,3,6,7-tetrahydro-2H-purin-2-oneYield 61.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

7-Benzyl-3-pentyl-3,7-dihydro-1H-purine-2,6-dione (2.0 g, 6.4 mmol) and phosphorus pentasulfide (3.0 g, 6.7 mmol) were mixed in 1,4-dioxane (20 mL). After stirring at 100° C. for 6 h, the reaction mixture was treated with a 2 M solution of sodium hydroxide in water (20 mL). Then the reaction mixture was adjusted to be acidic (pH ˜4) with 2 N HCl and extracted with EtOAc. The organic layer was concentrated, and the solid formed was washed with ether to provide the product as a yellow solid (1.30 g, 61.8% yield). LCMS calculated for C17H21N4OS (M+H): 329.1; found: 329.1.

Workup

  1. extractionextracted with EtOAc
  2. concentrationThe organic layer was concentrated
  3. customthe solid formed
  4. washwas washed with ether

Sources & evidence

ORD record
ord-8f81b79440ae4c04875f1c8f3dac7142
Source dataset
uspto-grants-2008_12
Patent number
US07462624B2

Reaction notes

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