1-Bromopropane → 3-Cyclopropyl-7-propylxanthine

HRID 2032

Reaction equation

HRID 2032 reaction equation
[CH:1]1([N:4]2[C:12]3[N:11]=[CH:10][NH:9][C:8]=3[C:7](=[O:13])[NH:6][C:5]2=[O:14])[CH2:3][CH2:2]1.[H-].[Na+].[H][H].Br[CH2:20][CH2:21][CH3:22]>CN(C)C=O>[CH:1]1([N:4]2[C:12]3[N:11]=[CH:10][N:9]([CH2:20][CH2:21][CH3:22])[C:8]=3[C:7](=[O:13])[NH:6][C:5]2=[O:14])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 78401-BromopropaneHCID 24758Sodium hydrideHCID 30589961H-Purine-2,6-dione, 3,7-dihydro-3-cyclopropyl-HCID 178418361HCID 178418361, compound

Product 1

HCID 196892703-Cyclopropyl-7-propylxanthine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

9.6 g (0.05 mol) of 3-cyclopropylxanthine were suspended in 150 ml of dimethylformamide and slowly deprotonated using 1.45 g (0.06 mol) of sodium hydride. When evolution of hydrogen was at an end, the solution was heated to 60° C. and treated dropwise with 6.77 g (0.055 mol) of bromopropane. After stirring at 70° C. for 3 hours, the solution was filtered, the dimethylformamide was evaporated under reduced pressure and the residue was crystallized from diisopropyl ether.

Workup

  1. filtrationthe solution was filtered
  2. customthe dimethylformamide was evaporated under reduced pressure
  3. customthe residue was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-8e167d88150f459d95e6145c9ec1c182
Source dataset
uspto-grants-1998_03
Patent number
US05728686

Linked notes

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