2,6-Dichloropyrazine → Ammonia

HRID 1593954Notes

Reaction equation

HRID 1593954 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][C@@H:12]2[CH2:14][C@H:9]1[CH2:10][NH:11]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:15][C:16]1[CH:21]=[N:20][CH:19]=[C:18](Cl)[N:17]=1>O1CCOCC1>[NH3:8].[Cl:15][C:16]1[N:17]=[C:18]([N:11]2[CH2:10][C@@H:9]3[CH2:14][C@H:12]2[CH2:13][N:8]3[C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH:19]=[N:20][CH:21]=1

Participants

5

Reactant 2

HCID 785042,6-DichloropyrazineHCID 11521263(1S,4S)-2-Boc-2,5-diazabicyclo[2.2.1]heptane

Product 2

HCID 222AmmoniaHCID 86598715HCID 86598715, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of tert-butyl-(1S,4S)-(+)-2,5-diazabicyclo-[2.2.1]-heptane-2-carboxylate (10.0 g, 50.4 mmol), 2,6-dichloropyrazine (15.0 g, 101 mmol) and dioxane (100 ml) was stirred at 40° C. for 3 days. The mixture was evaporated. Aqueous sodium hydroxide (100 ml, 1 M) was added, the mixture was evaporated to the half volume. The mixture was extracted with ethyl acetate (2×100 ml). Chromatography on silica gel with dichloromethane, methanol and conc. ammonia (89:10:1) gave the title compound as free base. Yield 11.6 g (73%).

Workup

  1. customThe mixture was evaporated
  2. additionAqueous sodium hydroxide (100 ml, 1 M) was added
  3. customthe mixture was evaporated to the half volume
  4. extractionThe mixture was extracted with ethyl acetate (2×100 ml)

Sources & evidence

ORD record
ord-58a3b7be981f45fda1796523aa9f7e5b
Source dataset
uspto-grants-2007_11
Patent number
US07300933B2

Reaction notes

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