Dimethyl Sulfoxide → Iodoethane

HRID 1044951Notes

Reaction equation

HRID 1044951 reaction equation
[CH2:1]([O:5][C:6]1[N:14]=[C:13]2[C:9]([N:10]=[C:11]([O:24]C)[N:12]2[CH2:15][CH2:16][CH2:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][NH:19]2)=[C:8]([NH2:26])[N:7]=1)[CH2:2][CH2:3][CH3:4].[CH3:27][CH2:28]N(C(C)C)C(C)C.[I:36][CH2:37][CH3:38].CS(C)=O>C(#N)C.CN(C=O)C.CO>[I:36][CH2:37][CH3:38].[NH2:26][C:8]1[N:7]=[C:6]([O:5][CH2:1][CH2:2][CH2:3][CH3:4])[N:14]=[C:13]2[C:9]=1[NH:10][C:11](=[O:24])[N:12]2[CH2:15][CH2:16][CH2:17][CH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][N:19]1[CH2:27][CH3:28]

Participants

9

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6340IodoethaneHCID 81531Diisopropylethylamine2×HCID 583061842-(Butyloxy)-8-(methyloxy)-9-[3-(2-piperidinyl)propyl]-9H-purin-6-amine

Product 2

HCID 6340IodoethaneHCID 67233766HCID 67233766, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent2×

Conditions

Temperature
50 °C

Procedure

A solution of 1-iodoethane was prepared by dissolving 1 mmole in acetonitrile (1 ml). A portion of this solution (0.12 ml, equivalent to 0.12 mmol) was added to a test tube. 2-(Butyloxy)-8-(methyloxy)-9-[3-(2-piperidinyl)propyl]-9H-purin-6-amine (435 mg, 1.2 mmol) was dissolved in DMF (6.0 ml) and an aliquot (0.5 ml, 0.1 mmole) dispensed to the tube. DIPEA (40 μL, 0.23 mmol) was added, and heated to 50° C. for 18 hours. An additional aliquot of 1-iodoethane in acetonitrile (80 uL, 0.08 mmol) (total added 0.2 mmol) and DIPEA (40 uL, 0.23 mmol) was added and continued stirring with heat at 50° C. for a further 18 hours. DMSO:MeOH (200 uL) was added, the mixture filtered and purified by Mass Directed AutoPrep (Method A). The solvent was evaporated in vacuo using the Genevac. The residue was redissolved in a solution of 4M HCl/dioxane (0.2 ml) and allowed to stand at room temperature for 4 hours. The solvent was dried under a stream of nitrogen in the Radleys blowdown apparatus. The material was redissolved in methanol (0.5 ml) and applied to an aminopropyl SPE (0.1 g, 3 ml, preconditioned in methanol (1.5 ml)). The product was eluted with additional methanol (1.5 ml). The solvent was removed to give the title compound (6 mg).

Workup

  1. additionA portion of this solution (0.12 ml, equivalent to 0.12 mmol) was added to a test tube
  2. temperaturewith heat at 50° C. for a further 18 hours
  3. filtrationthe mixture filtered
  4. custompurified by Mass Directed AutoPrep (Method A)
  5. customThe solvent was evaporated in vacuo
  6. dissolutionThe residue was redissolved in a solution of 4M HCl/dioxane (0.2 ml)
  7. customThe solvent was dried under a stream of nitrogen in the Radleys blowdown apparatus
  8. dissolutionThe material was redissolved in methanol (0.5 ml)
  9. washThe product was eluted with additional methanol (1.5 ml)
  10. customThe solvent was removed

Sources & evidence

ORD record
ord-5a1065fc754c4d19ac062c5e38fc3b75
Source dataset
uspto-grants-2013_10
Patent number
US08563717B2

Reaction notes

Loading…