Water → 7-Benzyl-3-methylxanthine

HRID 1814945Notes

Reaction equation

HRID 1814945 reaction equation
[OH-].[Na+].[CH3:3][N:4]1[C:12]2[N:11]=[CH:10][NH:9][C:8]=2[C:7](=[O:13])[NH:6][C:5]1=[O:14].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O>CO>[CH2:15]([N:9]1[C:8]2[C:7](=[O:13])[NH:6][C:5](=[O:14])[N:4]([CH3:3])[C:12]=2[N:11]=[CH:10]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 706393-Methylxanthine

Product 1

HCID 6856307-Benzyl-3-methylxanthineYield 69.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

A 10% aqueous sodium hydroxide solution (10 ml) was added to a suspension of 3-methylxanthine (4.15 g) in methanol (25 ml) and the mixture was stirred for 1 hour at 70° C. Benzyl bromide (4.275 g, 2.97 ml) was added dropwise at 70° C. and the mixture was stirred at 70-60° C. for an additional 5 hours. After cooling to room temperature, the mixture was treated with water (50 ml). The precipitate was filtered, dissolved in 1 N aqueous sodium hydroxide solution (50 ml) and the solution was acidified to pH 4-5 with concentrated hydrochloric acid. The precipitate was filtered and washed with water (3x 20 ml) to provide 7-benzyl-3-methylxanthine (4.45 g).

Workup

  1. stirringthe mixture was stirred at 70-60° C. for an additional 5 hours
  2. temperatureAfter cooling to room temperature
  3. filtrationThe precipitate was filtered
  4. dissolutiondissolved in 1 N aqueous sodium hydroxide solution (50 ml)
  5. filtrationThe precipitate was filtered
  6. washwashed with water (3x 20 ml)

Sources & evidence

ORD record
ord-3d0645b48ecc422f8766a164fef2ff4a
Source dataset
uspto-grants-2005_04
Patent number
US06878715B1

Reaction notes

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