Sodium Hydroxide → HCID 10934421, compound

HRID 2227354Notes

Reaction equation

HRID 2227354 reaction equation
[CH:1]1([C:4]2[NH:12][C:11]3[C:10](=O)[NH:9][C:8](=[S:14])[N:7]([CH2:15][CH2:16][CH3:17])[C:6]=3[N:5]=2)[CH2:3][CH2:2]1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:19].[OH-].[Na+]>N1C=CC=CC=1>[CH:1]1([C:4]2[NH:12][C:11]3[C:10](=[S:19])[NH:9][C:8](=[S:14])[N:7]([CH2:15][CH2:16][CH3:17])[C:6]=3[N:5]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 14817Phosphorus sulfide (P2S5)HCID 10890332HCID 10890332, compound

Product 1

HCID 10934421HCID 10934421, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In a 5 L 3-necked flask fitted with a mechanical stirrer and a condenser with a drying tube were placed 2.2 L of pyridine and 8-cyclopropyl-3-propyl-2-thio-xanthine (220 g, 0.88 mol). Phosphorus pentasulfide (236 g, 1.06 mol) was added and the mixture was heated under reflux for 5 hours and stored overnight at room temperature. The reaction mixture was cooled to 5-10° and 3 N aqueous sodium hydroxide (770 ml) was added over 1.5 hours with stirring. Stirring was continued for 30 minutes after removal of the cooling bath and the precipitated product was collected by suction filtration. The filter cake was washed successively with pyridine (300 ml) and four 300 ml portions of tetrahydrofuran. The solvents are evaporated in vacuo and the solid residue was stirred with water (750 ml), filtered and washed with water. The crude product was dissolved in 1.7 L of 1 N sodium hydroxide and stirred with 15 g of Darco G-60. The charcoal was filtered and the treatment was repeated with a fresh portion of charcoal. The solution was acidified to pH 1.5 with 6 N hydrochloric acid and the pale yellow precipitate was collected. The solid was dissolved again in 1.7 L of 1N sodium hydroxide and treated successively with two portions of charcoal as above. The solution was acidified and the precipitate was collected and washed with water. After drying to constant weight at 54° C. under vacuum, there was obtained 128 g (56%) of the title compound, mp over 245° C.

Workup

  1. customIn a 5 L 3-necked flask fitted with a mechanical stirrer and a condenser with a drying tube
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 5 hours
  4. temperatureThe reaction mixture was cooled to 5-10°
  5. stirringStirring
  6. waitwas continued for 30 minutes
  7. customafter removal of the cooling bath
  8. filtrationthe precipitated product was collected by suction filtration
  9. washThe filter cake was washed successively with pyridine (300 ml) and four 300 ml portions of tetrahydrofuran
  10. customThe solvents are evaporated in vacuo
  11. stirringthe solid residue was stirred with water (750 ml)
  12. filtrationfiltered
  13. washwashed with water
  14. dissolutionThe crude product was dissolved in 1.7 L of 1 N sodium hydroxide
  15. stirringstirred with 15 g of Darco G-60
  16. filtrationThe charcoal was filtered
  17. customthe pale yellow precipitate was collected
  18. dissolutionThe solid was dissolved again in 1.7 L of 1N sodium hydroxide
  19. additiontreated successively with two portions of charcoal as above
  20. customthe precipitate was collected
  21. washwashed with water
  22. customAfter drying to constant weight at 54° C. under vacuum

Sources & evidence

ORD record
ord-f530231e9df045d387f05109f5847403
Source dataset
uspto-grants-2002_07
Patent number
US06413975B1

Reaction notes

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