Methyl iodide → Xanthine
Reaction equation
C([N:5]1[C:13]2[N:12]=[CH:11][N:10](CCCCC(=O)C)[C:9]=2[C:8](=[O:21])[NH:7][C:6]1=[O:22])CCC.[OH-].[Na+].CI>CO.O>[NH:7]1[C:8](=[O:21])[C:9]2[NH:10][CH:11]=[N:12][C:13]=2[NH:5][C:6]1=[O:22]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 48 °C
Procedure
60 g of 3-n-butyl-7-(5'-oxohexyl)-xanthine are added to a solution of 8 g of sodium hydroxide in 160 ml of a methanol/water mixture (1:1). 28 g of methyl iodide are dropwise added to the clear solution having a temperature of 40° C. and the mixture is stirred at 48° C. for 24 hours. After concentration under reduced pressure the residue is diluted with 300 ml of diethylether and the unreacted 3-(n-butyl)-7-(5'-oxohexyl)-xanthine is removed by shaking with 1 N sodium hydroxide. After neutralisation, drying, concentration under reduced pressure and distillation at 140° C. temperature of the mixture and 0.02 mmHg 48.5 g of 1-methyl-3-(n-butyl)-7-(5'-oxohexyl)-xanthine are obtained from the ether phase as a viscous oil (nD20 =1.5320; yield 77.2%, referred to reacted starting xanthine). Analysis: C16H24N4O3 =320.396
Workup
- customa temperature of 40° C.
- concentrationAfter concentration under reduced pressure the residue
- additionis diluted with 300 ml of diethylether
- customthe unreacted 3-(n-butyl)-7-(5'-oxohexyl)-xanthine is removed
- stirringby shaking with 1 N sodium hydroxide
- customAfter neutralisation, drying
- concentrationconcentration
- distillationunder reduced pressure and distillation at 140° C. temperature of the mixture and 0.02 mmHg 48.5 g of 1-methyl-3-(n-butyl)-7-(5'-oxohexyl)-xanthine
Sources & evidence
- ORD record
- ord-340ee89fafbb4a95b229b4386130b1d0
- Source dataset
- uspto-grants-1981_09
- Patent number
- US04289776
Reaction notes
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