HCID 53804992, compound → 3-Methylxanthine

HRID 1814961Notes

Reaction equation

HRID 1814961 reaction equation
C(O[C@@H](C)CCCC[N:10]1[C:19](=[O:20])[C:18]2[N:17](CC3C=CC=CC=3)[C:16](CO)=[N:15][C:14]=2[N:13]([CH3:30])[C:11]1=[O:12])(=O)C>S(Cl)(Cl)=O>[CH3:30][N:13]1[C:14]2[N:15]=[CH:16][NH:17][C:18]=2[C:19](=[O:20])[NH:10][C:11]1=[O:12]

Participants

3

Reactant 1

HCID 53804992HCID 53804992, compound

Product 1

HCID 706393-MethylxanthineYield 228.7%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

To a solution of thionyl chloride (100 ml) was added (S)-1-(5-acetoxyhexyl)-7-benzyl-8-hydroxymethyl-3-methylxanthine (9.8 g, 22.9 mmol). After stirring for 3 hours at room temperature, unreacted thionyl chloride was evaporated under reduced pressure. The residual oil was purled by flash chromatography on silica gel eluting with ethyl acetate-hexane (1:1) to afford (S)-1-(5-acetoxyhexyl)-7-benzyl-8-chloromethyl(-3-methylxanthine (8.7 g, 85% yield) as a colorless oil.

Workup

  1. customunreacted thionyl chloride was evaporated under reduced pressure

Sources & evidence

ORD record
ord-e2ec31e06d31450d93008f7a8d356345
Source dataset
uspto-grants-2005_04
Patent number
US06878715B1

Reaction notes

Loading…