Sodium Hydroxide → HCID 10198198, compound

HRID 429788Notes

Reaction equation

HRID 429788 reaction equation
[CH2:1]([N:3]1[C:11]2[N:10]=[C:9]([CH2:12][CH3:13])[NH:8][C:7]=2[C:6](=O)[N:5]=[CH:4]1)[CH3:2].P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:16].[OH-].[Na+]>N1C=CC=CC=1>[CH2:1]([N:3]1[C:11]2[N:10]=[C:9]([CH2:12][CH3:13])[NH:8][C:7]=2[C:6](=[S:16])[N:5]=[CH:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 14817Phosphorus sulfide (P2S5)HCID 9837011HCID 9837011, compound

Product 1

HCID 10198198HCID 10198198, compoundYield 63.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The product of stage (i) (8.65 g) and phosphorus pentasulfide (12.0 g) was refluxed in 150 ml of pyridine for 1 hr. Under cooling 59.4 ml of 2N NaOH was added dropwise, the solid filtered off and washed with water. The filtrate was concentrated in vacuo to dryness and the residue suspended in 200 ml of water and collected. The filtrate was extracted three times with 600 ml of chloroform. The residue of the organic phase was combined with the solid collected (total 6.08 g), dissolved in 500 ml of chloroform and filtered through 24 g of silicagel. Fractions 2 and 3 eluted 4.63 g of crude product which was crystallized from 120 ml of methanol to give 3,8-diethyl-6-thiohypoxanthine (3.58 g) with mp (sublimation at 210° C.) 250-270° C. under decomposition A second crop gave 0.58 g.

Workup

  1. additionwas added dropwise
  2. filtrationthe solid filtered off
  3. washwashed with water
  4. concentrationThe filtrate was concentrated in vacuo to dryness
  5. customcollected
  6. extractionThe filtrate was extracted three times with 600 ml of chloroform
  7. customcollected (total 6.08 g)
  8. dissolutiondissolved in 500 ml of chloroform
  9. filtrationfiltered through 24 g of silicagel
  10. washFractions 2 and 3 eluted 4.63 g of crude product which
  11. customwas crystallized from 120 ml of methanol

Sources & evidence

ORD record
ord-af0636615a5b4de39fe4b7d083d41d1a
Source dataset
uspto-grants-2001_11
Patent number
US06319928B1

Reaction notes

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