Sodium Hydroxide → HCID 15462262, compound

HRID 2305383Notes

Reaction equation

HRID 2305383 reaction equation
[CH:1]([C:4]1[NH:12][C:11]2[C:10](=O)[NH:9][C:8](=[O:14])[N:7]([CH2:15][C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[C:6]=2[N:5]=1)([CH3:3])[CH3:2].P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:23].[OH-].[Na+]>N1C=CC=CC=1>[CH:1]([C:4]1[NH:12][C:11]2[C:10](=[S:23])[NH:9][C:8](=[O:14])[N:7]([CH2:15][C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[C:6]=2[N:5]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 14817Phosphorus sulfide (P2S5)HCID 15462261HCID 15462261, compound

Product 1

HCID 15462262HCID 15462262, compoundYield 136.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
5 °C

Procedure

1.19 g of 8-isopropyl-3-(4-picolyl)-xanthine and 1.07 g of phosphorus pentasulfide were heated under reflux in 25 ml of pyridine for 4 hours. After cooling to 5° C., 5.28 ml (10.6 mM) of 2N NaOH were added. The solid was filtered off and washed with pyridine. The filtrate was evaporated to dryness, the residue suspended in water and the solid collected, redissolved in 40 ml of 1N NaOH, treated with 0.2 g of charcoal, filtered and neutralized to pH 7.5. The solid was collected, washed and dried to give the title compound (0.99 g) as a white solid mp 310-14° C. (decomposition);

Workup

  1. filtrationThe solid was filtered off
  2. washwashed with pyridine
  3. customThe filtrate was evaporated to dryness
  4. customthe solid collected
  5. dissolutionredissolved in 40 ml of 1N NaOH
  6. additiontreated with 0.2 g of charcoal
  7. filtrationfiltered
  8. customThe solid was collected
  9. washwashed
  10. customdried

Sources & evidence

ORD record
ord-76a259fcc92b4332bdefc6b7a0dd7180
Source dataset
uspto-grants-2002_08
Patent number
US06440979B1

Reaction notes

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