Iodoethane → HCID 87978311, compound

HRID 1063261Notes

Reaction equation

HRID 1063261 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([CH2:16][CH3:17])[C:5]([NH:10][C@@H:11]([CH2:14][CH3:15])[CH2:12][OH:13])=[N:6][C:7]=1[CH2:8][CH3:9].[H-].[Na+].I[CH2:21][CH3:22]>CN(C=O)C>[Br:1][C:2]1[N:3]=[C:4]([CH2:16][CH3:17])[C:5]([NH:10][C@H:11]([CH2:12][O:13][CH2:21][CH3:22])[CH2:14][CH3:15])=[N:6][C:7]=1[CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 6340Iodoethane2×HCID 24758Sodium hydride2×HCID 87951597HCID 87951597, compound

Product 1

HCID 87978311HCID 87978311, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A dry 50 mL round bottom flask was charged with a solution of (2S)-2-[(5-bromo-3,6-diethylpyrazin-2-yl)amino]butan-1-ol (356 mg, 1.18 mmol) in DMF (12 mL). NaH (70.8 mg, 1.77 mmol) was added to the homogeneous solution. Effervescence was observed and the solution turned cloudy. Iodoethane (0.189 mL, 2.36 mmol) was added at once. The now yellow solution was stirred at ambient temperature for 20 minutes. The same quantities of NaH and iodoethane were added to the reaction mixture two more times in the same manner. The reaction was quenched with water and extracted twice with ethyl acetate. The organics were combined, dried with Na2SO4, filtered and concentrated to give 510 mg of a crude yellow oil. This material was purified by Biotage MPLC (90 g column, using 5% ethyl acetate in heptane) to give 193 mg (50%) of 5-bromo-N-[(1S)-1-(ethoxymethyl)propyl]-3,6-diethylpyrazin-2-amine as a yellow oil. Rf 0.16 (5% ethyl acetate in heptane).

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted twice with ethyl acetate
  3. dry with materialdried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give 510 mg of a crude yellow oil
  7. customThis material was purified by Biotage MPLC (90 g column, using 5% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-ef563e6c5a214af48f9792323c571f4e
Source dataset
uspto-grants-2005_11
Patent number
US06964965B2

Reaction notes

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