Sodium Hydroxide → 3-[(4-Chlorophenyl)methyl]-1,3,6,9-tetrahydro-6-thioxo-2H-purin-2-one

HRID 2305380Notes

Reaction equation

HRID 2305380 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][N:7]2[C:15]3[N:14]=[CH:13][NH:12][C:11]=3[C:10](=O)[NH:9][C:8]2=[O:17])=[CH:4][CH:3]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:21].[OH-].[Na+]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][N:7]2[C:15]3[N:14]=[CH:13][NH:12][C:11]=3[C:10](=[S:21])[NH:9][C:8]2=[O:17])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 14817Phosphorus sulfide (P2S5)HCID 15462259HCID 15462259, compound

Product 1

HCID 154622603-[(4-Chlorophenyl)methyl]-1,3,6,9-tetrahydro-6-thioxo-2H-purin-2-oneYield 134.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
10 °C

Procedure

11.06 g of 3-(4-chlorobenzyl)-xanthine and 11.34 g of phosphorus pentasulfide were heated under reflux in 112 ml of pyridine for 4 hours. After cooling to 10° C., 52 ml of 2N NaOH were added over 30 minutes. The mixture was evaporated to dryness, the residue suspended in 120 ml of water and the pH adjusted to 7.5. The solid was collected, redissolved in 150 ml of 1N NaOH, treated with 0.6 g of charcoal, filtered and neutralized to pH 7.0. The solid was collected again to give the title compound (10.07 g) mp 313-7° C.;

Workup

  1. customThe mixture was evaporated to dryness
  2. customThe solid was collected
  3. dissolutionredissolved in 150 ml of 1N NaOH
  4. additiontreated with 0.6 g of charcoal
  5. filtrationfiltered
  6. customThe solid was collected again

Sources & evidence

ORD record
ord-9bf41976c5014a09a80edd7adaa323f4
Source dataset
uspto-grants-2002_08
Patent number
US06440979B1

Reaction notes

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