Chloropyrazine → HCID 57227784, compound

HRID 2260805

Reaction equation

HRID 2260805 reaction equation
[CH3:1][N:2]1[CH2:7][C@@H:6]2[CH2:8][C@H:3]1[CH2:4][NH:5]2.Cl[C:10]1[CH:15]=[N:14][CH:13]=[CH:12][N:11]=1>C(Cl)Cl>[CH3:1][N:2]1[CH2:7][C@@H:6]2[CH2:8][C@H:3]1[CH2:4][N:5]2[C:10]1[CH:15]=[N:14][CH:13]=[CH:12][N:11]=1

Participants

4

Reactant 2

HCID 73277ChloropyrazineHCID 11029795(1S,4S)-2-Methyl-2,5-diazabicyclo[2.2.1]heptane

Product 1

HCID 57227784HCID 57227784, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 2.1 g of (S,S)-2-methyl-2,5-diazabicyclo[2.2.1]heptane prepared by the procedure of U. Jordis et al, Synthesis, 1990, 925, and 1.8 ml of 2-chloropyrazine in 8 ml of diazabicyclo[3.6.0]undecene-5 is heated to approximately 80° C. for 2 hours. The reaction solution is cooled, diluted with 100 ml of methylene chloride and washed with 30 ml of 5N aqueous sodium hydroxide. The organic layer is dried and concentrated in vacuo to dryness. The residue is purified by chromatography (aluminum oxide, Activity Grade 2.5; methylene chloride to 5% methyl alcohol/methylene chloride) to give 2.1 g of the desired product as a pale yellow oil:

Workup

  1. temperatureThe reaction solution is cooled
  2. washwashed with 30 ml of 5N aqueous sodium hydroxide
  3. customThe organic layer is dried
  4. concentrationconcentrated in vacuo to dryness
  5. customThe residue is purified by chromatography (aluminum oxide, Activity Grade 2.5; methylene chloride to 5% methyl alcohol/methylene chloride)

Sources & evidence

ORD record
ord-19199d6472b0477a9985a98b6cfa98b2
Source dataset
uspto-grants-1995_12
Patent number
US05478939

Linked notes

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