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Ethanolamine → 2-((6-Chloropyrazin-2-yl)amino)ethanol

HRID 1774750
Notes
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Reaction equation

HRID 1774750 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1.[NH2:9][CH2:10][CH2:11][OH:12].CCN(C(C)C)C(C)C>C(O)CCC>[Cl:8][C:4]1[N:3]=[C:2]([NH:9][CH2:10][CH2:11][OH:12])[CH:7]=[N:6][CH:5]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 700EthanolamineHCID 785042,6-DichloropyrazineHCID 81531Diisopropylethylamine

Product 1

HCID 534088382-((6-Chloropyrazin-2-yl)amino)ethanolYield 50%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
80 °C
On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Procedure

In a sealed tube, 2,6-dichloropyrazine (1 g, 6.71 mmol) was mixed with 2-aminoethanol (0.492 g, 8.05 mmol), Hunig's base (1.13 g, 8.73 mmol) in BuOH (7 mL) and the reaction mixture was heated to 80° C. over night. The mixture was concentrated in vacuo and the residue partitioned between NaHCO3 (20 mL) and EtOAc (100 mL). The organic phase was separated, washed with brine, dried over Na2SO4, filtered and evaporated to dryness to give the title compound (0.583 g, 50%) as a light yellow foam. MS: 174.1 (M+H+).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue partitioned between NaHCO3 (20 mL) and EtOAc (100 mL)
  3. customThe organic phase was separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-0651662b5f2445acb5803f7bbfa2290b
Source dataset
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09260408B2

Reaction notes

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