Trifluoroacetic acid → HCID 59299531, compound

HRID 2386628Notes

Reaction equation

HRID 2386628 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](COCC[Si](C)(C)C)[C:4]=2[N:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[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

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59299565HCID 59299565, compound

Product 1

HCID 59299531HCID 59299531, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 8-chloro-1-methyl-7-(2-propen-1-yl)-3-({[2-(trimethylsilyl)ethyl]oxy}methyl)-3,7-dihydro-1H-purine-2,6-dione (2.99 g, 8.08 mmol) in DCM (20 ml) was added TFA (10 ml) and the reaction stirred for 2.5 hours at room temperature. The reaction mixture was then concentrated and the residue treated with further DCM and evaporated once more. Purification by SPE (Si) eluting 1:9-4:1 ethylacetate/cyclohexane afforded impure product (1.31 g), which was dissolved in methanol (20 ml) and treated with sat. potassium carbonate aq. (20 ml). After stirring overnight the mixture was partitioned between water containing 2M HCl (1 ml) and ethyl acetate. The organic extract was separated, washed with brine, dried (MgSO4) and concentrated to afford the title compound 0.87 g (45%); m/z 241.1 [MH+].

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. additionthe residue treated with further DCM
  3. customevaporated once more
  4. customPurification by SPE (Si)
  5. washeluting 1:9-4:1 ethylacetate/cyclohexane afforded impure product (1.31 g), which
  6. dissolutionwas dissolved in methanol (20 ml)
  7. additiontreated with sat. potassium carbonate aq. (20 ml)
  8. stirringAfter stirring overnight the mixture
  9. customwas partitioned between water containing 2M HCl (1 ml) and ethyl acetate
  10. extractionThe organic extract
  11. customwas separated
  12. washwashed with brine
  13. dry with materialdried (MgSO4)
  14. concentrationconcentrated

Sources & evidence

ORD record
ord-1b65d38b94e84f51a2eb9e1fcebc1eac
Source dataset
uspto-grants-2012_09
Patent number
US08268839B2

Reaction notes

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