Sodium Hydroxide → HCID 9943273, compound

HRID 1600833Notes

Reaction equation

HRID 1600833 reaction equation
[CH2:1]([N:3]1[C:12](=O)[C:11]2[NH:10][C:9]([CH:14]([CH3:16])[CH3:15])=[N:8][C:7]=2[N:6]([CH2:17][CH3:18])[C:4]1=[O:5])[CH3:2].P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:20].[OH-].[Na+]>N1C=CC=CC=1>[CH2:1]([N:3]1[C:12](=[S:20])[C:11]2[NH:10][C:9]([CH:14]([CH3:16])[CH3:15])=[N:8][C:7]=2[N:6]([CH2:17][CH3:18])[C:4]1=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 14817Phosphorus sulfide (P2S5)HCID 21715761HCID 21715761, compound

Product 1

HCID 9943273HCID 9943273, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

1,3-diethyl-8-isopropyl-xanthine (6.25 g, 25 mM) (J Amer Chem Soc 1953, 75, 114-5) and 6.8 g (30 mM) of phosphorus pentasulfide were refluxed in 86 ml of pyridine for 3 days. At 10-20° C., 33.5 ml of 2N NaOH are added with cooling. The solid was filtered off and washed with pyridine. The filtrate was evaporated in vacuo to dryness, the residue suspended in 50 ml of water, adjusted to pH 7.5, the solid collected, washed with water and dried. The product was redissolved in 30 ml NaOH, treated twice with 0.5 g of charcoal, filtered, and acidified with 5N HCl to pH 3. At 5° C., the solid was collected, washed and dried.

Workup

  1. temperaturewith cooling
  2. filtrationThe solid was filtered off
  3. washwashed with pyridine
  4. customThe filtrate was evaporated in vacuo to dryness
  5. customthe solid collected
  6. washwashed with water
  7. customdried
  8. dissolutionThe product was redissolved in 30 ml NaOH
  9. additiontreated twice with 0.5 g of charcoal
  10. filtrationfiltered
  11. customAt 5° C., the solid was collected
  12. washwashed
  13. customdried

Sources & evidence

ORD record
ord-3f61c2ce8e5741698768f3e136763978
Source dataset
uspto-grants-1999_11
Patent number
US05977119

Reaction notes

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