Acetic Acid → 2-(Methylsulfanyl)pyrimidine-5-carbonitrile

HRID 1827249Notes

Reaction equation

HRID 1827249 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]([S:10][CH3:11])[N:3]=1.C(O)(=O)C>C(O)C.O.[Zn]>[CH3:11][S:10][C:4]1[N:5]=[CH:6][C:7]([C:8]#[N:9])=[CH:2][N:3]=1

Participants

6

Reactant 2

HCID 176Acetic AcidHCID 131141834-Chloro-2-(methylsulfanyl)pyrimidine-5-carbonitrile

Product 1

HCID 131141842-(Methylsulfanyl)pyrimidine-5-carbonitrile

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred mixture of 4-chloro-2-(methylthio)pyrimidine-5-carbonitrile (0.843 g, 4.54 mmol) and zinc dust (1.48 g, 22.71 mmol) in ethanol (7.5 mL) and water (1.4 mL) was slowly added acetic acid (0.29 mL, 5.13 mmol). The resulting reaction mixture was vigorously stirred for 3 h. The solids were removed by filtration and the filtrate concentrated in vacuo. The residue was chromatographed on silica gel 60 (35 g), eluting with 10:1–20:89–70 CH2Cl2:2-propanol:hexane to give the title compound. M.S. (M+1): 152.

Workup

  1. customThe resulting reaction mixture
  2. customThe solids were removed by filtration
  3. concentrationthe filtrate concentrated in vacuo
  4. customThe residue was chromatographed on silica gel 60 (35 g)
  5. washeluting with 10:1–20:89–70 CH2Cl2

Sources & evidence

ORD record
ord-c3c87187bbef49c0b53e6f18314bd67c
Source dataset
uspto-grants-2006_05
Patent number
US07053089B2

Reaction notes

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