Methyl(2-phenoxyethyl)amine → 3-Chloro-N-methyl-N-(2-phenoxyethyl)-2-pyrazinamine

HRID 991625Notes

Reaction equation

HRID 991625 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[N:6][CH:5]=[CH:4][N:3]=1.[CH3:9][NH:10][CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C=O)C>[Cl:8][C:7]1[C:2]([N:10]([CH3:9])[CH2:11][CH2:12][O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:3][CH:4]=[CH:5][N:6]=1

Participants

4

Reactant 2

HCID 37732Methyl(2-phenoxyethyl)amineHCID 785752,3-Dichloropyrazine

Product 1

HCID 220364993-Chloro-N-methyl-N-(2-phenoxyethyl)-2-pyrazinamineYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2,3-dichloropyrazine (6.64 g, 44.6mmol) and N-methyl-N-(2-phenoxyethyl)amine* (4.5 g, 29.8 mmol) in DMF (5 mL) was placed in a sealed Pyrex tube and heated in a microwave oven (Labwell MW10) for 1×2 min followed by 2×1 min at 75W. The mixture was concentrated and the resulting oil was purified by column chromatography on silica using hexane/EtOAc (95:5 followed by 93:7) to give 5.56 g (71%) of the title product as a colorless oil. HRMS m/z calcd for C13H14ClN3O (M)+ 263.0825, found 263.0824.

Workup

  1. customwas placed in a sealed Pyrex tube
  2. temperatureheated in a microwave oven (Labwell MW10) for 1×2 min
  3. concentrationThe mixture was concentrated
  4. customthe resulting oil was purified by column chromatography on silica

Sources & evidence

ORD record
ord-89a45d0b181542c0aa582a8ccf5b6b23
Source dataset
uspto-grants-2002_10
Patent number
US06465467B1

Reaction notes

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