3-Chloro-2,5-dimethylpyrazine → HCID 178430524, compound

HRID 744051Notes

Reaction equation

HRID 744051 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[N:8]=[CH:7][NH:6][CH:5]=1.Cl[C:10]1[C:15]([CH3:16])=[N:14][CH:13]=[C:12]([CH3:17])[N:11]=1>CC(O)C>[NH:6]1[CH:5]=[C:4]([CH2:3][CH2:2][NH:1][C:10]2[C:15]([CH3:16])=[N:14][CH:13]=[C:12]([CH3:17])[N:11]=2)[N:8]=[CH:7]1

Participants

4

Reactant 2

HCID 667713-Chloro-2,5-dimethylpyrazineHCID 178419017HCID 178419017, compound

Product 1

HCID 178430524HCID 178430524, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

1 g (8.9 mmol) of histamine and 1.28 g (8.9 mmol) of 2-chloro-3,6-dimethylpyrazine in 10 ml of 2-propanol are brought to reflux for 3 days, evaporated and the residue is chromatographed on a column of silica gel, using mixtures of chloroform and methanol (1, 10 and 20% respectively) to give the title compound in the form of an oil. The latter is converted to a monohydrated dioxalate salt which is crystallized from an isopropanol/ether (1/1) mixture. M.p.: 164°-165° C.

Workup

  1. temperatureto reflux for 3 days
  2. customevaporated
  3. customthe residue is chromatographed on a column of silica gel

Sources & evidence

ORD record
ord-e8e0e667cd4c499786a44301ebd2bda3
Source dataset
uspto-grants-1996_09
Patent number
US05559113

Reaction notes

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