Sodium Carbonate → 8-chloro-7-(2-propen-1-yl)-3-propyl-3,7-dihydro-1H-purine-2,6-dione

HRID 1097654

Reaction equation

HRID 1097654 reaction equation
[Cl:1][C:2]1[N:10]([CH2:11][CH:12]=[CH2:13])[C:9]2[C:8](=[O:14])[NH:7][C:6](=[O:15])[NH:5][C:4]=2[N:3]=1.I[CH2:17][CH2:18][CH3:19].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C>[Cl:1][C:2]1[N:10]([CH2:11][CH:12]=[CH2:13])[C:9]2[C:8](=[O:14])[NH:7][C:6](=[O:15])[N:5]([CH2:17][CH2:18][CH3:19])[C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 336431-IodopropaneHCID 592995327-Allyl-8-chloro-1H-purine-2,6(3H,7H)-dione

Product 1

HCID 592995678-chloro-7-(2-propen-1-yl)-3-propyl-3,7-dihydro-1H-purine-2,6-dioneYield 46.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 8-chloro-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione (1.5 g, 6.6 mmol), 1-iodopropane (1.2 g, 6.9 mmol) and sodium carbonate (0.9 g, 8.5 mmol) in DMF (40 ml) was heated at 50° C. for 18 h. The reaction mixture was concentrated in vacuo and the residue treated with water (60 ml) and extracted with EtOAc (3×80 ml). The combined organic extracts were dried (MgSO4) filtered and evaporated. The residue was triturated with ether/cyclohexane, the solid was filtered off and dried to afford the title compound (0.82 g, 46%).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionthe residue treated with water (60 ml)
  3. extractionextracted with EtOAc (3×80 ml)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was triturated with ether/cyclohexane
  8. filtrationthe solid was filtered off
  9. customdried

Sources & evidence

ORD record
ord-e83b300d5b9f4568ba6a382636f15bc3
Source dataset
uspto-grants-2012_03
Patent number
US08143264B2

Linked notes

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