Chloro-N,N-dimethylformiminium chloride → HCID 86758757, compound

HRID 2300829Notes

Reaction equation

HRID 2300829 reaction equation
[C:1]1([C@@H:7]([NH:9][C:10]2[N:15]=[C:14](O)[CH:13]=[C:12]([CH3:17])[N:11]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl-].[Cl:19]C=[N+](C)C>C(Cl)(Cl)Cl>[C:1]1([C@@H:7]([NH:9][C:10]2[N:15]=[C:14]([Cl:19])[CH:13]=[C:12]([CH3:17])[N:11]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 77311Chloro-N,N-dimethylformiminium chlorideHCID 178429400HCID 178429400, compound

Product 1

HCID 86758757HCID 86758757, compoundYield 18.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 2-[(S)-1-phenylethylamino]-4-hydroxy-6-methylpyrimidine (100 mg, 0.436 mmol, 1 eq) in chloroform (2 mL) was added (chloromethylene)dimethylammonium chloride (Vilsmeier reagent) (55.9 mg, 0.436 mmol, 1 eq). After 1 hour the solvent was removed under reduced pressure. The product was purified by silica gel chromatography (eluted with 3:1 hexanes/acetone) to give 19.8 mg of the title compound. Mass spectrum (NH3/CI): 248.1 (M+1).

Workup

  1. customAfter 1 hour the solvent was removed under reduced pressure
  2. customThe product was purified by silica gel chromatography (eluted with 3:1 hexanes/acetone)

Sources & evidence

ORD record
ord-5cf85c33e23544ce9db7a4d7b9f663e9
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

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