Sodium Carbonate → 8-chloro-7-(2-propen-1-yl)-3-(4,4,4-trifluorobutyl)-3,7-dihydro-1H-purine-2,6-dione

HRID 1943788Notes

Reaction equation

HRID 1943788 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.C(=O)([O-])[O-].[Na+].[Na+].Br[CH2:23][CH2:24][CH2:25][C:26]([F:29])([F:28])[F:27]>CN(C)C=O>[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]([CH2:23][CH2:24][CH2:25][C:26]([F:29])([F:28])[F:27])[C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 5210064-Bromo-1,1,1-trifluorobutaneHCID 592995327-Allyl-8-chloro-1H-purine-2,6(3H,7H)-dione

Product 1

HCID 592995888-chloro-7-(2-propen-1-yl)-3-(4,4,4-trifluorobutyl)-3,7-dihydro-1H-purine-2,6-dioneYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

8-chloro-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione (1.5 g, 6.64 mmol), sodium carbonate (844 mg, 7.9 mmol) and 4-bromo-1,1,1-trifluorobutane (1.39 g, 7.3 mmol) were stirred in dimethylformamide (25 ml, dry) for seven days. The reaction mixture was partitioned between ethyl acetate and water. The organic phase was separated and washed with hydrochloric acid (2N), brine, dried (MgSO4) and then evaporated to dryness. The crude product was triturated with ether and the solid collected by filtration to afford 8-chloro-7-(2-propen-1-yl)-3-(4,4,4-trifluorobutyl)-3,7-dihydro-1H-purine-2,6-dione as a white solid (1.23 g, 57%). m/z 337 [MH+].

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. customThe organic phase was separated
  3. washwashed with hydrochloric acid (2N), brine
  4. dry with materialdried (MgSO4)
  5. customevaporated to dryness
  6. customThe crude product was triturated with ether
  7. filtrationthe solid collected by filtration

Sources & evidence

ORD record
ord-656b2e8d506c47bbbfb85672688a4e7d
Source dataset
uspto-grants-2013_03
Patent number
US08394808B2

Reaction notes

Loading…