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Ethanolamine → 3-Bromo-5-[(2-hydroxyethyl)amino]-2-pyrazinecarbonitrile

HRID 1838210
Notes
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Reaction equation

HRID 1838210 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].[Br:5][C:6]1[C:7]([C:13]#[N:14])=[N:8][CH:9]=[C:10](Cl)[N:11]=1.C(N(C(C)C)C(C)C)C>O1CCOCC1>[Br:5][C:6]1[C:7]([C:13]#[N:14])=[N:8][CH:9]=[C:10]([NH:4][CH2:3][CH2:1][OH:2])[N:11]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 700EthanolamineHCID 81531DiisopropylethylamineHCID 187532003-Bromo-5-chloropyrazine-2-carbonitrile

Product 1

HCID 187532053-Bromo-5-[(2-hydroxyethyl)amino]-2-pyrazinecarbonitrileYield 53.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

0.061 g (1.00 mmol) of ethanolamine were added slowly at room temperature to a solution of 0.218 g (1.0 mmol) of the 3-bromo-5-chloro-pyrazine-2-carbonitrile and 0.264 g (2.0 mmol) of N-ethyldiisopropylamine in 15.0 ml of dioxane. The reaction mixture was stirred at room temperature for 18 hours. It was subsequently poured into 50 ml of an ice/water/sodium hydrogen carbonate mixture and extracted 3 times with 50 ml of ethylacetate. The combined ethylacetate phases were dried over magnesium sulfate and evaporated under reduced pressure. The residue formed was chromatographed on silica gel with a 100:0 to 95:5 v/v gradient of dichloromethane and methanol as the eluent giving 0.131 g (0.539 mmol, 53.9% of theory) of the 3-bromo-5-(2-hydroxy-ethylamino)-pyrazine-2-carbonitrile as yellow solid; m.p. 158-160° C.; MS: 243 (M)+.

Workup

  1. extractionextracted 3 times with 50 ml of ethylacetate
  2. dry with materialThe combined ethylacetate phases were dried over magnesium sulfate
  3. customevaporated under reduced pressure
  4. customThe residue formed
  5. customwas chromatographed on silica gel with a 100:0 to 95:5 v/v gradient of dichloromethane and methanol as the eluent

Sources & evidence

ORD record
ord-90174f5ca9494acd9f1906a2531a3133
Source dataset
uspto-grants-2004_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06673795B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes