Chloro-N,N-dimethylformiminium chloride → 4-Chloro-2-(ethylsulfanyl)pyrimidine-5-carbonitrile

HRID 2300824

Reaction equation

HRID 2300824 reaction equation
[CH2:1]([S:3][C:4]1[N:9]=[C:8](O)[C:7]([C:11]#[N:12])=[CH:6][N:5]=1)[CH3:2].[Cl-].[Cl:14]C=[N+](C)C>O1CCOCC1>[CH2:1]([S:3][C:4]1[N:9]=[C:8]([Cl:14])[C:7]([C:11]#[N:12])=[CH:6][N:5]=1)[CH3:2]

Participants

4

Reactant 2

HCID 77311Chloro-N,N-dimethylformiminium chlorideHCID 178477341HCID 178477341, compound

Product 1

HCID 183753954-Chloro-2-(ethylsulfanyl)pyrimidine-5-carbonitrileYield 60.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-ethylthio-4-hydroxy-5-cyanopyrimidine (196 mg, 1.08 mmol) in 1,4-dioxane (5 mL) was added (chloro-methylene)dimethylammonium chloride (550 mg, 4.32 mmol). The mixture was heated at 100° C. for 4 h, cooled, and the solvent was removed under reduced pressure. The crude material was purified by flash chromatography using 1:20 acetone:hexane system to yield 130 mg of the title compound. Mass spectrum 199.3 (EI, M+).

Workup

  1. temperaturecooled
  2. customthe solvent was removed under reduced pressure
  3. customThe crude material was purified by flash chromatography

Sources & evidence

ORD record
ord-24b5f1748416463f96734d0ff44993bb
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Linked notes

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