Chloro-N,N-dimethylformiminium chloride → 2-Ethylthio4-chloro-6-propylpyrimidine

HRID 2300831Notes

Reaction equation

HRID 2300831 reaction equation
[CH2:1]([S:3][C:4]1[N:9]=[C:8](O)[CH:7]=[C:6]([CH2:11][CH2:12][CH3:13])[N:5]=1)[CH3:2].[Cl-].[Cl:15]C=[N+](C)C>C(Cl)(Cl)Cl>[CH2:1]([S:3][C:4]1[N:9]=[C:8]([Cl:15])[CH:7]=[C:6]([CH2:11][CH2:12][CH3:13])[N:5]=1)[CH3:2]

Participants

4

Reactant 2

HCID 77311Chloro-N,N-dimethylformiminium chlorideHCID 178439472HCID 178439472, compound

Product 1

HCID 183758132-Ethylthio4-chloro-6-propylpyrimidineYield 85.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To the solution of 2-ethylthio-4-hydroxy-6-propylpyrimidine (406 mg) in CHCl3 (6 mL) was added (chloromethylene)-dimethylammonium chloride (Villsmier reagent) (786 mg). The reaction was stirred at room temperature under nitrogen for 40 min. Filtration through silica gel followed by removal of solvent provided 380 mg of the title compound as yellowish oil. 1H NMR (500 MHz, CDCl3): δ 6.81 (s, 1H); 3.17 (q, J=7.3 Hz, 2H); 2.65 (t, J=7.5 Hz, 2H); 1.76 (m, J=7.6 Hz, 2H); 1.41 (t, J=7.3 Hz, 3H); 0.99 (t, J=7.3 Hz, 3H).

Workup

  1. filtrationFiltration through silica gel
  2. customfollowed by removal of solvent

Sources & evidence

ORD record
ord-841bd56371f240a5b392cc46881b7c51
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

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