Potassium Carbonate → 7-(2-butyn-1-yl)-3,7-dihydro-3-methyl-1H-Purine-2,6-dione

HRID 1792008Notes

Reaction equation

HRID 1792008 reaction equation
[CH3:1][N:2]1[C:10]2[N:9]=[CH:8][NH:7][C:6]=2[C:5](=[O:11])[NH:4][C:3]1=[O:12].C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][C:21]#[C:22][CH3:23]>CN(C)C=O.C(OCC)(=O)C>[CH2:20]([N:7]1[C:6]2[C:5](=[O:11])[NH:4][C:3](=[O:12])[N:2]([CH3:1])[C:10]=2[N:9]=[CH:8]1)[C:21]#[C:22][CH3:23]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 706393-MethylxanthineHCID 27568621-Bromo-2-butyne

Product 1

HCID 220293647-(2-butyn-1-yl)-3,7-dihydro-3-methyl-1H-Purine-2,6-dione

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Methylxanthine (1.1 g) was dissolved in N,N-dimethylformamide (15 ml), and potassium carbonate (1.0 g) and 1-bromo-2-butyne (0.64 ml) were added thereto. After stirring at room temperature overnight, the reaction mixture was diluted with ethyl acetate, and washed with water. Insoluble white solid was collected by filtration, and washed with ethyl acetate to give 1.3 g of 7-(2-butynyl)-3-methyl-3,7-dihydropurine-2,6-dione. Then, the resulting 7-(2-butynyl)-3-methyl-3,7-dihydropurine-2,6-dione (1.3 g) was dissolved in N,N-dimethylformamide (15 ml), and N-chlorosuccinimide (0.89 g) was added while cooling on ice. After stirring at room temperature for 3 hours, the reaction mixture was diluted with ethyl acetate, and washed with water. Insoluble white solid was collected by filtration, and washed with ethyl acetate to give 1.1 g of 7-(2-butynyl)-8-chloro-3-methyl-3,7-dihydropurine-2,6-dione. The resulting 7-(2-butynyl)-8-chloro-3-methyl-3,7-dihydropurine-2,6-dione (1.4 g) and 1-piperazine carboxylic acid tert-butyl ester (2.8 g) were stirred at 150° C. for 1 hour. After cooling to room temperature, the reaction mixture was extracted with ethyl acetate, then the organic layer was washed with water and saturate brine, and was dried over anhydrous magnesium sulfate. The solvent was removed by distillation at reduced pressure. The residue was purified by silica gel column chromatography to obtain 1.1 g of the title compound from a fraction eluted with hexane-ethyl acetate (1:4).

Workup

  1. washwashed with water
  2. filtrationInsoluble white solid was collected by filtration
  3. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-c57168f093724e30ac4695ae5b8c804d
Source dataset
uspto-grants-2006_07
Patent number
US07074798B2

Reaction notes

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