Hydrogen Sulfide → HCID 15172927, compound

HRID 2082282Notes

Reaction equation

HRID 2082282 reaction equation
I[C:2]1[N:3]=[C:4]([NH2:20])[C:5]2[N:6]=[CH:7][N:8]([C:18]=2[N:19]=1)[C@@H:9]1[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:10]1[OH:11].C(N(CC)CC)C.[CH:28]1([C:34]#[CH:35])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.S>CN(C)C=O.C(Cl)(Cl)Cl.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:28]1([C:34]#[C:35][C:2]2[N:3]=[C:4]([NH2:20])[C:5]3[N:6]=[CH:7][N:8]([C:18]=3[N:19]=2)[C@@H:9]2[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:10]2[OH:11])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

8

Reactant 4

HCID 402Hydrogen SulfideHCID 8471TriethylamineHCID 70263EthynylcyclohexaneHCID 1696622-Iodoadenosine

Product 1

HCID 15172927HCID 15172927, compoundYield 59%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

1.95 g (5 mmol) of 2-iodoadenosine was dissolved in 20 ml of N,N-dimethylformamide (DMF), to which were added 0.18 g of bis(triphenylphosphine)palladium dichloride, 0.1 g of cuprous iodide, 2.8 ml of triethylamine and 0.8 ml of cyclohexylacetylene. The resulting mixture was stirred at a temperature of 90° C. for two hours. The reaction solution after being allowed to cool, was concentrated to dryness. The residue obtained was dissolved in chloroform, into which was vigorously introduced hydrogen sulfide gas over one minute. The solution was then dried under reduced pressure. The residue was purified by silica gel column chromatography, followed by recrystallization from ethanol-water, thereby obtaining 1.11 g (2.97 mmol) of crystalline 2-(cyclohexylethynyl)adenosine (yield: 59%).

Workup

  1. temperatureto cool
  2. concentrationwas concentrated to dryness
  3. customThe residue obtained
  4. customover one minute
  5. customThe solution was then dried under reduced pressure
  6. customThe residue was purified by silica gel column chromatography
  7. customfollowed by recrystallization from ethanol-water

Sources & evidence

ORD record
ord-3be1cadb397148ceb0f25c75e36e5a23
Source dataset
uspto-grants-1993_02
Patent number
US05189027

Reaction notes

Loading…