Methyl iodide → Xanthobine

HRID 1754585Notes

Reaction equation

HRID 1754585 reaction equation
[Br:1][C:2]1[NH:10][C:9]2[C:8](=[O:11])[NH:7][C:6](=O)[N:5]([CH3:13])[C:4]=2[N:3]=1.[CH3:14]I.[C:16](=[O:19])([O-])[O-].[K+].[K+]>CN(C)C=O.O>[Br:1][C:2]1[N:10]([CH3:14])[C:9]2[C:8](=[O:11])[N:7]([CH3:6])[C:16](=[O:19])[N:5]([CH3:13])[C:4]=2[N:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 15487978-bromo-3-methyl-3,7-dihydro-1H-purine-2,6-dione

Product 1

HCID 64127Xanthobine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 8-bromo-3-methyl xanthine (300 mg; 1.2 mmol) and methyl iodide (1.42 g; 10.0 mmol) in N,N-dimethylformamide (5 ml) was added to potassium carbonate (662 mg; 4.8 mmol) and was heated to 60° C. for 6 hrs. The reaction mixture was poured in water (25 ml) and extracted with ethyl acetate (3×25 ml). The combined extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The product was purified by flash chromatography over silica gel eluting with ethyl acetate to yield the desired product. 315 mg; 92% PRO-04-45

Workup

  1. extractionextracted with ethyl acetate (3×25 ml)
  2. extractionThe combined extract
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe product was purified by flash chromatography over silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-c261131c51f64b10a72372ceb4d21ba8
Source dataset
uspto-grants-2015_10
Patent number
US09169255B2

Reaction notes

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