Water → 8-Bromo-7-(2-butyn-1-yl)-3,7-dihydro-3-methyl-1H-purine-2,6-dione

HRID 1773321Notes

Reaction equation

HRID 1773321 reaction equation
[Br:1][C:2]1[NH:10][C:9]2[C:8](=[O:11])[NH:7][C:6](=[O:12])[N:5]([CH3:13])[C:4]=2[N:3]=1.C(N(CC)C(C)C)(C)C.Br[CH2:24][C:25]#[C:26][CH3:27].O>CN(C)C=O>[CH3:13][N:5]1[C:4]2[N:3]=[C:2]([Br:1])[N:10]([CH2:24][C:25]#[C:26][CH3:27])[C:9]=2[C:8](=[O:11])[NH:7][C:6]1=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 15487978-bromo-3-methyl-3,7-dihydro-1H-purine-2,6-dioneHCID 27568621-Bromo-2-butyne

Product 1

HCID 210889278-Bromo-7-(2-butyn-1-yl)-3,7-dihydro-3-methyl-1H-purine-2,6-dioneYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

By utilizing the well known method, 8-bromo-3-methyl-xanthine (5 g, 20.4 mmol) was dissolved in N,N-dimethylformamide (30 ml). N,N-diisopropylethylamine (2.633 g, 20.4 mmol) and 1-bromo-2-butyne (2.714 g, 20.4 mmol) were added to obtain a reaction mixture. The reaction mixture was reacted overnight at room temperature and TLC was used to monitor the reaction progress. After the reaction was completed, the obtained reaction mixture was poured into water, suction filtered, and the obtained solid was washed with water for three times, dried to give 3-methyl-7-(2-butyn-1-yl)-8-bromo-xanthine 1a (5.15 g, light yellow solid), yield: 85%.

Workup

  1. customto obtain a reaction mixture
  2. customThe reaction mixture was reacted overnight at room temperature
  3. customthe obtained reaction mixture
  4. filtrationfiltered
  5. washthe obtained solid was washed with water for three times
  6. customdried

Sources & evidence

ORD record
ord-458117b89d4446e8849050ef89dbe7f1
Source dataset
uspto-grants-2016_02
Patent number
US09255098B2

Reaction notes

Loading…