Tetrahydrofuran → 2-(Methylthio)-4-pyrimidinecarbonitrile

HRID 499551Notes

Reaction equation

HRID 499551 reaction equation
Cl[C:2]1[N:7]=[CH:6][CH:5]=[C:4]([C:8]#[N:9])[N:3]=1.[CH3:10][S-:11].[Na+].C1COCC1.C(OCC)(=O)C>O>[C:8]([C:4]1[N:3]=[C:2]([S:11][CH3:10])[N:7]=[CH:6][CH:5]=1)#[N:9]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 2466472-Chloropyrimidine-4-carbonitrileHCID 4378561Sodium methanethiolate

Product 1

HCID 2957772-(Methylthio)-4-pyrimidinecarbonitrileYield 66%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-chloro-6-cyanopyrimidine (2.20 g, 15.8 mmol), sodium thiomethoxide (1.22 g, 17.3 mmol) and THF (100 ml) was refluxed for 2 hrs. The reaction mixture was combined with ethyl acetate and water. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated to give the titled compound (1.57 g, 66%) as pale yellow crystals.

Workup

  1. temperaturewas refluxed for 2 hrs
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-2a0bab44120a4abd906c72099472a2ae
Source dataset
uspto-grants-2010_08
Patent number
US07767665B2

Reaction notes

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