Acrylonitrile → HCID 15160070, compound

HRID 1089313Notes

Reaction equation

HRID 1089313 reaction equation
[C@@H:1]1([N:10]2[CH:15]=[C:14]3[CH:16]=[CH:17][C:18](=[O:20])[N:19]=[C:13]3[NH:12][C:11]2=[O:21])[O:7][C@H:6]([CH2:8][OH:9])[C@@H:4]([OH:5])[C@H:2]1[OH:3].[C:22]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.C(#N)C=C>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C@@H:1]1([N:10]2[CH:15]=[C:14]3[CH:16]=[CH:17][C:18](=[O:20])[N:19]([CH3:22])[C:13]3=[N:12][C:11]2=[O:21])[O:7][C@H:6]([CH2:8][OH:9])[C@@H:4]([OH:5])[C@H:2]1[OH:3]

Participants

7

Reactant 4

HCID 7855AcrylonitrileHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 178515721HCID 178515721, compound

Product 1

HCID 15160070HCID 15160070, compoundYield 396.6%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Procedure

A solution was prepared by dissolving 460 mg of 5-iododeoxyuridine (a) in 20 ml of absolute dioxane, to which 22 mg of palladium acetate, 34 mg of triphenylphosphine, 0.3 ml of triethylamine, and 0.13 ml of acrylonitrile were added and the mixture was made to undergo a reaction at 100° C. for 12 hours. After the removal of the precipitate by filtration, a hydrogen sulfide gas bubbled into the filtrate and the resulting precipitate was removed by filtration with Calite. The filtrate was concentrated under reduced pressure and the residue was refined by column chromatography on silica gel to obtain 159 mg of (E)-5-(2-cyanoethenyl)deoxyuridine (b).

Workup

  1. customA solution was prepared
  2. customa reaction at 100° C. for 12 hours
  3. customAfter the removal of the precipitate
  4. filtrationby filtration
  5. customa hydrogen sulfide gas bubbled into the filtrate
  6. customthe resulting precipitate was removed by filtration with Calite
  7. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3b05fae740c34d30ac3c3852050cc426
Source dataset
uspto-grants-1990_10
Patent number
US04965350

Reaction notes

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