2-(Dimethylamino)ethanol → 2-[(5-Bromopyrazin-2-yl)oxy]-N,N-dimethylethan-1-amine

HRID 1465576Notes

Reaction equation

HRID 1465576 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][OH:5].CC(C)([O-])C.[Na+].[Br:13][C:14]1[CH:19]=[N:18][C:17](Br)=[CH:16][N:15]=1>C1COCC1.C(OCC)(=O)C>[Br:13][C:14]1[N:15]=[CH:16][C:17]([O:5][CH2:4][CH2:3][N:2]([CH3:6])[CH3:1])=[N:18][CH:19]=1

Participants

6

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 114704212,5-dibromopyrazineHCID 23676156Sodium t-butoxide

Product 1

HCID 467381972-[(5-Bromopyrazin-2-yl)oxy]-N,N-dimethylethan-1-amineYield 88%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(dimethylamino)ethanol (28-1, 8.00 g, 78.9 mmol) in THF (100 mL) was added sodium tert-butoxide (10.0 g, 102.0 mmol) at room temperature. The reaction was stirred for 15 min. The reaction mixture was cooled to 0° C. and added with a solution of 2,5-dibromopyrazine (28-2, 20.0 g, 82.4 mmol) in THF (100 ml) slowly in a period of 5.0 min. The reaction mixture was warmed to room temperature and stirred for 16 h. The mixture was diluted with ethyl acetate and washed with saturated NH4Cl. The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure to give 2-((5-bromopyrazin-2-yl)oxy)-N,N-dimethylethanamine (28-3, 17.0 g) as yellow oils in 88% yield: 1H NMR (500 MHz, CDCl3) δ 8.46 (s, 1 H), 8.16 (d, J=1.1 Hz, 1 H), 8.06 (d, J=1.1 Hz, 1 H), 4.68 (t, J=4.8 Hz, 2 H), 3.20 (s, 2 H), 2.70 (s, 6 H).

Workup

  1. temperatureThe reaction mixture was warmed to room temperature
  2. stirringstirred for 16 h
  3. washwashed with saturated NH4Cl
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-10002cab2c9c4d9b9555295d33392617
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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