1,4-Dioxane → 5-Cyano-4-(3-methoxyphenyl)-2-methylthio-6-vinyl-pyrimidine

HRID 1766080Notes

Reaction equation

HRID 1766080 reaction equation
Cl[C:2]1[N:7]=[C:6]([S:8][CH3:9])[N:5]=[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=2)[C:3]=1[C:18]#[N:19].O1CCO[CH2:22][CH2:21]1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:18]([C:3]1[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=2)=[N:5][C:6]([S:8][CH3:9])=[N:7][C:2]=1[CH:21]=[CH2:22])#[N:19]

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 3558104-Chloro-6-(3-methoxyphenyl)-2-(methylthio)pyrimidine-5-carbonitrile

Product 1

HCID 211090865-Cyano-4-(3-methoxyphenyl)-2-methylthio-6-vinyl-pyrimidine

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

6-Chloro-5-cyano-4-(3-methoxyphenyl)-2-methylthio-pyrimidine (example 1b, 1.46 g) was suspended in 1,4-dioxane (10 ml). Tetrakis(triphenylphosphine)palladium(0) (350 mg) was added and the mixture was flushed with a nitrogen atmosphere. Tetravinyltin (1.26 ml) was added and the mixture was refluxed for 5 h. The reaction mixture was then poured in a mixture of EtOAc (100 ml) and H2O (100 ml). The organic layer was washed with sat. aq. NaCl, dried (MgSO4) and concentrated under reduced pressure. The title compound was purified by chromatography on silica gel with hept/CH2Cl2=1/0 to 1/3 (v/v).

Workup

  1. customthe mixture was flushed with a nitrogen atmosphere
  2. additionTetravinyltin (1.26 ml) was added
  3. temperaturethe mixture was refluxed for 5 h
  4. additionThe reaction mixture was then poured in a mixture of EtOAc (100 ml) and H2O (100 ml)
  5. washThe organic layer was washed with sat. aq. NaCl
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated under reduced pressure
  8. customThe title compound was purified by chromatography on silica gel with hept/CH2Cl2=1/0 to 1/3 (v/v)

Sources & evidence

ORD record
ord-72b7594f4fac4bb29da706aaa1f9e52b
Source dataset
uspto-grants-2007_06
Patent number
US07229990B2

Reaction notes

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