Iodoethane → HCID 326140, compound

HRID 1943841Notes

Reaction equation

HRID 1943841 reaction equation
[Cl:1][C:2]1[N:10](CC=C)[C:9]2[C:8](=[O:14])[N:7]([CH3:15])[C:6](=[O:16])[NH:5][C:4]=2[N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:23](I)[CH3:24].N1CCOCC1>CN(C=O)C.CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[NH:10][C:9]2[C:8](=[O:14])[N:7]([CH3:15])[C:6](=[O:16])[N:5]([CH2:23][CH3:24])[C:4]=2[N:3]=1

Participants

8

Reactant 4

HCID 6340IodoethaneHCID 8083MorpholineHCID 10340Sodium CarbonateHCID 59299531HCID 59299531, compound

Product 1

HCID 326140HCID 326140, compoundYield 70%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 8-chloro-1-methyl-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione (100 mg, 0.42 mmol) in anhydrous DMF (3 ml) was added sodium carbonate (58 mg, 0.54 mmol), after 10 minutes stirring ethyl iodide (0.043 ml, 0.54 mmol) was added and the reaction mixture stirred at room temperature under nitrogen for 90 hours. Pd(PPh3)4 (73 mg, 0.063 mmol) was then added and the reaction vessel evacuated and flushed with nitrogen (×3), morpholine (0.37 ml, 4.3 mmol) was added and stirring at room temperature under nitrogen continued for 4 hours. The reaction mixture was diluted with EtOAc (25 ml) and washed with 2M HCl aq. (25 ml). The organic extract was dried (MgSO4) filtered and evaporated. Purification by aminopropyl SPE (5 g) loading the compound and washing with MeOH before eluting the product with 5% AcOH/MeOH afforded the title compound as a white solid (67 mg, 70%). NMR; dH (400 MHz, d6-DMSO) 1.20 (t, 3H, J=7 Hz), 3.22 (s, 3H), 3.97 (q, 2H, J=7 Hz), 14.46 (1H, br s); m/z 227.2[M−H]−.

Workup

  1. additionwas added
  2. customthe reaction vessel evacuated
  3. additionwas added
  4. stirringstirring at room temperature under nitrogen
  5. waitcontinued for 4 hours
  6. washwashed with 2M HCl aq. (25 ml)
  7. extractionThe organic extract
  8. dry with materialwas dried (MgSO4)
  9. filtrationfiltered
  10. customevaporated
  11. customPurification by aminopropyl SPE (5 g)
  12. washwashing with MeOH
  13. washbefore eluting the product with 5% AcOH/MeOH

Sources & evidence

ORD record
ord-5c89c6f6ca6747198ddae284558e6017
Source dataset
uspto-grants-2013_03
Patent number
US08394808B2

Reaction notes

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