Toluene → 3,6-Diethyl-N-(pentan-3-yl)pyrazin-2-amine

HRID 1063255Notes

Reaction equation

HRID 1063255 reaction equation
Cl[C:2]1[C:7]([CH2:8][CH3:9])=[N:6][CH:5]=[C:4]([CH2:10][CH3:11])[N:3]=1.C1(C)C=CC=CC=1.[CH2:19]([CH:21]([NH2:24])[CH2:22][CH3:23])[CH3:20].CC(C)([O-])C.[Na+]>C([O-])(O)=O.[Na+].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>[CH2:8]([C:7]1[C:2]([NH:24][CH:21]([CH2:22][CH3:23])[CH2:19][CH3:20])=[N:3][C:4]([CH2:10][CH3:11])=[CH:5][N:6]=1)[CH3:9]

Participants

7

Reactant 4

HCID 1140TolueneHCID 120193-PentanamineHCID 2373953-Chloro-2,5-diethylpyrazineHCID 23676156Sodium t-butoxide

Product 1

HCID 222787563,6-Diethyl-N-(pentan-3-yl)pyrazin-2-amineYield 84%

Reagents, catalysts & solvents 2

HCID 27342152-(Di-tert-butylphosphino)biphenylCatalystHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
100 °C

Procedure

A 250 mL dry round bottom flask equipped with a magnetic stir bar and reflux condenser was charged with 2-chloro-3,6-diethylpyrazine (9.22 g, 54 mmol), dry toluene (108 mL), 1-ethyl propylamine (12.6 mL, 108 mmol), 2-(di-tert-butylphosphino)biphenyl (0.966 g, 3.24 mmol), sodium tert-butoxide (7.26 g, 75.6 mmol), and tris (dibenzylidineacetone)dipalladium (0) (1.48 g, 1.62 mmol) respectively. The mixture was heated to 100° C. for 4 hours. After cooling to ambient temperature, the reaction was poured in saturated aqueous NaHCO3 and extracted twice with ethyl acetate. The organics were combined, dried with Na2SO4, filtered and concentrated to 14.1 g of a dark crude oil. The crude was purified by Biotage MPLC in two batches (120 g columns, 10% ethyl acetate in heptane.) Like fractions were combined to give 10.0 g (84%) of 3,6-diethyl-N-(1-ethylpropyl)pyrazin-2-amine as an orange oil.

Workup

  1. customA 250 mL dry round bottom flask
  2. customequipped with a magnetic stir bar
  3. temperaturereflux condenser
  4. temperatureAfter cooling to ambient temperature
  5. extractionextracted twice with ethyl acetate
  6. dry with materialdried with Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated to 14.1 g of a dark crude oil
  9. customThe crude was purified by Biotage MPLC in two batches (120 g columns, 10% ethyl acetate in heptane.) Like fractions

Sources & evidence

ORD record
ord-d7697ebd1b12479084ce8935c0882f71
Source dataset
uspto-grants-2005_11
Patent number
US06964965B2

Reaction notes

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