Hydrochloric Acid → HCID 59299531, compound

HRID 1943809Notes

Reaction equation

HRID 1943809 reaction equation
[Cl:1][C:2]1[N:10]([CH2:11][CH:12]=[CH2:13])[C:9]2[C:8](=[O:14])[N:7]([CH3:15])[C:6](=[O:16])[N:5](COCCOC)[C:4]=2[N:3]=1.Cl>O1CCOCC1.O>[Cl:1][C:2]1[N:10]([CH2:11][CH:12]=[CH2:13])[C:9]2[C:8](=[O:14])[N:7]([CH3:15])[C:6](=[O:16])[NH:5][C:4]=2[N:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59299571HCID 59299571, compound

Product 1

HCID 59299531HCID 59299531, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 8-chloro-1-methyl-3-({[2-(methyloxy)ethyl]oxy}methyl)-7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione (2.9 g, 6.37 mmol) in dioxan (20 ml) and water (20 ml) was added 5M HCl (20 ml). The resulting mixture was heated at 100° C. under nitrogen for 18 hours. The reaction mixture was then concentrated in vacuo, the residue was dissolved in EtOAc (100 ml) and washed with water. The organic extract was dried (MgSO4) filtered and evaporated. Purification by SPE (Si, 20 g) eluting 2:3 EtOAc/cyclohexane afforded the title compound as a white solid (1.04 g, 68%). m/z 241.1[MH+].

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. dissolutionthe residue was dissolved in EtOAc (100 ml)
  3. washwashed with water
  4. extractionThe organic extract
  5. dry with materialwas dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customPurification by SPE (Si, 20 g)
  9. washeluting 2:3 EtOAc/cyclohexane

Sources & evidence

ORD record
ord-2fcd4a65479f47cc94369084a94e3116
Source dataset
uspto-grants-2013_03
Patent number
US08394808B2

Reaction notes

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