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

HRID 2386607Notes

Reaction equation

HRID 2386607 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+].CS(O[CH2:27][CH2:28][CH:29]1[CH2:31][CH2:30]1)(=O)=O>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]([CH2:27][CH2:28][CH:29]3[CH2:31][CH2:30]3)[C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 145578092-Cyclopropylethyl methanesulfonateHCID 592995327-Allyl-8-chloro-1H-purine-2,6(3H,7H)-dione

Product 1

HCID 592995418-chloro-3-(2-cyclopropylethyl)-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dioneYield 49.1%

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 2-cyclopropylethyl methanesulfonate (1.19 g, 7.3 mmol) were stirred in dimethylformamide (25 ml, dry) for two days at 80° C. 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 the title compound as a white solid (0.96 g, 49%). m/z 295 [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-ab6193fd14044c439c02da201ea2c766
Source dataset
uspto-grants-2012_09
Patent number
US08268839B2

Reaction notes

Loading…