N-Iodosuccinimide → 3,6-diethyl-N-(1-ethylpropyl)-5-iodopyrazin-2-amine

HRID 1063275Notes

Reaction equation

HRID 1063275 reaction equation
[CH2:1]([C:3]1[C:4]([NH:11][CH:12]([CH2:15][CH3:16])[CH2:13][CH3:14])=[N:5][C:6]([CH2:9][CH3:10])=[CH:7][N:8]=1)[CH3:2].C1C(=O)N([I:24])C(=O)C1>CN(C=O)C>[CH2:1]([C:3]1[C:4]([NH:11][CH:12]([CH2:15][CH3:16])[CH2:13][CH3:14])=[N:5][C:6]([CH2:9][CH3:10])=[C:7]([I:24])[N:8]=1)[CH3:2]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 222787563,6-Diethyl-N-(pentan-3-yl)pyrazin-2-amine

Product 1

HCID 222786973,6-diethyl-N-(1-ethylpropyl)-5-iodopyrazin-2-amineYield 74%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3,6-diethyl-N-(1-ethylpropyl)pyrazin-2-amine, NIS (5.37 g, 23.9 mmol) and anhydrous DMF (100 mL) under N2 was heated at 50° C. for 4 h. The solution was partitioned between ethyl acetate and H2O and separated. The aqueous phase was extracted with ethyl acetate and the combined organics were washed with H2O, brine and dried (MgSO4). The mixture was filtered and concentrated to give a brown oil which was purified by flash chromatography (20% ethyl acetate in heptane) to give 5.57 g (74%) of 3,6-diethyl-N-(1-ethylpropyl)-5-iodopyrazin-2-amine as a light brown oil. 1H NMR (400 MHz, CDCl3) δ 4.02 (m, 2 H), 2.76 (q, 2 H), 2.57 (q, 2 H), 1.60-1.70 (m, 2 H), 1.45-1.55 (m, 2 H) 1.20-1.30 (m, 6 H), 0.92 (q, 6 H).

Workup

  1. customThe solution was partitioned between ethyl acetate and H2O
  2. customseparated
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. washthe combined organics were washed with H2O, brine
  5. dry with materialdried (MgSO4)
  6. filtrationThe mixture was filtered
  7. concentrationconcentrated
  8. customto give a brown oil which
  9. customwas purified by flash chromatography (20% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-a33b9554da2a4d299e46328b20aa4354
Source dataset
uspto-grants-2005_11
Patent number
US06964965B2

Reaction notes

Loading…