Sodium Hydroxide → HCID 15462258, compound

HRID 1108224Notes

Reaction equation

HRID 1108224 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:25]=[CH:26][C:27]=2[O:28][CH3:29])[CH2:10][N:11]2[C:19]3[N:18]=[C:17]([CH:20]([CH3:22])[CH3:21])[NH:16][C:15]=3[C:14](=O)[NH:13][C:12]2=[O:24])[CH2:5][CH2:4][CH2:3][CH2:2]1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:31].[OH-].[Na+]>N1C=CC=CC=1>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:25]=[CH:26][C:27]=2[O:28][CH3:29])[CH2:10][N:11]2[C:19]3[N:18]=[C:17]([CH:20]([CH3:22])[CH3:21])[NH:16][C:15]=3[C:14](=[S:31])[NH:13][C:12]2=[O:24])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 14817Phosphorus sulfide (P2S5)HCID 15462257HCID 15462257, compound

Product 1

HCID 15462258HCID 15462258, compoundYield 151%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3.59 g of 3-(3-cyclopentyloxy-4-methoxy-benzyl)-8-isopropyl-xanthine and 2.40 g of phosphorus pentasulfide were heated under reflux in 60 ml of pyridine for 8 hours. At -5° C., 11.9 ml of 2N NaOH were added slowly. The suspension was evaporated to dryness, the residue suspended in 100 ml of water, neutralized to pH 8, and the solid, collected, washed and dried to give the crude 6-thioxanthine (3.45 g). Purification by filtration chromatography (SiO2, 15 g; chloroform) yielded a solid which was reprecipitated from NaOH by addition of HCl, to pH 6.5, collected, washed and dried to give the monohydrate of the title compound (3.38 g) as a white solid, mp 192-3° C.

Workup

  1. customThe suspension was evaporated to dryness
  2. customthe solid, collected
  3. washwashed
  4. customdried
  5. customto give the crude 6-thioxanthine (3.45 g)
  6. customPurification
  7. filtrationby filtration chromatography (SiO2, 15 g; chloroform)
  8. customyielded a solid which
  9. customwas reprecipitated from NaOH by addition of HCl, to pH 6.5
  10. customcollected
  11. washwashed
  12. customdried

Sources & evidence

ORD record
ord-7e7b430ccaa04966b2ddbf212084c826
Source dataset
uspto-grants-2000_05
Patent number
US06066641

Reaction notes

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