Propionitrile → HCID 12151210, compound

HRID 2415031Notes

Reaction equation

HRID 2415031 reaction equation
Cl[C:2]1[C:7]([I:8])=[C:6]([C:9]([F:12])([F:11])[F:10])[N:5]=[C:4]([S:13][CH3:14])[N:3]=1.[C:15](#[N:18])CC>CN(C)C1C=CN=CC=1>[C:15]([C:2]1[C:7]([I:8])=[C:6]([C:9]([F:12])([F:11])[F:10])[N:5]=[C:4]([S:13][CH3:14])[N:3]=1)#[N:18]

Participants

4

Reactant 2

HCID 7854PropionitrileHCID 121514194-chloro-5-iodo-2-methylthio-6-trifluoromethylpyrimidine

Product 1

HCID 12151210HCID 12151210, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

4-Chloro-5-iodo-2-methylthio-6-trifluoromethylpyrimidine (5.00 g) was dissolved in propionitrile (125 ml) and 4-(dimethylamino)-pyridine (1.81 g) was added at room temperature with stirring. After several minutes, precipitates appeared, however, it was stirred over night at room temperature. The slurry was cooled to ice bath temperature, and then added sodium cyanide (1.04 g) water (10 ml) solution. The mixture was warmed to room temperature and stirred 3 hr. The reaction mixture was added water and extracted with ethyl acetate. The ethyl acetate layer was washed with water and brine, respectively and dried over magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by silica get column chromatography (hexane-ethyl acetate) to give 4-cyano-5-iodo-2-methylthio-6-trifluoromiethylpyrimidine (2.56 g) as yellow solid, mp 68-69° C.

Workup

  1. waitAfter several minutes
  2. customprecipitates
  3. stirringhowever, it was stirred over night at room temperature
  4. temperatureThe slurry was cooled to ice bath temperature
  5. stirringstirred 3 hr
  6. additionThe reaction mixture was added water
  7. extractionextracted with ethyl acetate
  8. washThe ethyl acetate layer was washed with water and brine
  9. dry with materialrespectively and dried over magnesium sulfate
  10. customThe solvent was removed under reduced pressure
  11. customThe residue was purified by silica
  12. customget column chromatography (hexane-ethyl acetate)
  13. customto give 4-cyano-5-iodo-2-methylthio-6-trifluoromiethylpyrimidine (2.56 g) as yellow solid, mp 68-69° C.

Sources & evidence

ORD record
ord-30b9ecbffa8249bfb88cdb22d480dbfb
Source dataset
uspto-grants-2004_11
Patent number
US06818631B1

Reaction notes

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