Phosphorus sulfide (P2S5) → 8-(4-Hydroxy-bicyclo[2.2.2]oct-1-yl)-3-propyl-6-thioxo-1,3,6,7-tetrahydro-purin-2-one

HRID 395275Notes

Reaction equation

HRID 395275 reaction equation
[OH:1][C:2]12[CH2:9][CH2:8][C:5]([C:10]3[NH:18][C:17]4[C:16](=O)[NH:15][C:14](=[O:20])[N:13]([CH2:21][CH2:22][CH3:23])[C:12]=4[N:11]=3)([CH2:6][CH2:7]1)[CH2:4][CH2:3]2.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:25]>N1C=CC=CC=1>[OH:1][C:2]12[CH2:9][CH2:8][C:5]([C:10]3[NH:18][C:17]4[C:16](=[S:25])[NH:15][C:14](=[O:20])[N:13]([CH2:21][CH2:22][CH3:23])[C:12]=4[N:11]=3)([CH2:6][CH2:7]1)[CH2:4][CH2:3]2

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 11994283HCID 11994283, compound

Product 1

HCID 119956538-(4-Hydroxy-bicyclo[2.2.2]oct-1-yl)-3-propyl-6-thioxo-1,3,6,7-tetrahydro-purin-2-oneYield 19%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

8-(4-Hydroxy-bicyclo[2.2.2]oct-1-yl)-3-propyl-3,7-dihydro-purine-2,6-dione (500 mg, 1.57 mmol) was dissolved in 10 mL of pyridine. P4S10 (1.05 g, 1.5 eq) was added and the reaction mixture was stirred under reflux for 6 h. The reaction mixture was then cooled to rt and quenched slowly with 5 mL of H2O. The mixture was then acidified at 0° C. to pH 5 with 6 N HCl. The aqueous layer was extracted with EtOAc. The combined organic layer was dried (Na2SO4) and concentrated under reduced pressure. Purification by preparative HPLC afforded 100 mg of the titled compound.

Workup

  1. temperatureunder reflux for 6 h
  2. customquenched slowly with 5 mL of H2O
  3. customwas then acidified at 0° C. to pH 5 with 6 N HCl
  4. extractionThe aqueous layer was extracted with EtOAc
  5. dry with materialThe combined organic layer was dried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-c499d584c769481088eb1dba97848fcd
Source dataset
uspto-grants-2003_08
Patent number
US06605601B2

Reaction notes

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