Benzylamine → N-Benzyl-6-chloropyrazin-2-amine

HRID 1296624Notes

Reaction equation

HRID 1296624 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1.[CH2:9]([NH2:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C.ClCCl>[CH2:9]([NH:16][C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 7504BenzylamineHCID 11430Potassium CarbonateHCID 785042,6-Dichloropyrazine

Product 1

HCID 11708350N-Benzyl-6-chloropyrazin-2-amineYield 81%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 2,6-dichloropyrazine (1.31 g, 8.8 mmol), benzylamine (1.15 g, 10.7 mmol) and K2CO3 (1.65 g, 11.9 mmol) in acetonitrile (6 mL) was heated at 85° C. for 13 h in a sealed pyrex flask. The reaction mixture was diluted with dichloromethane, filtered and concentrated in vacuo. The yellow solid residue was dissolved in a small volume of methanol and purified by silica gel chromatography (18×4 cm) using CHCl3/MeOH (98:2) as eluent. A second purification (SiO2; 16×4 cm) using CHCl3 as eluent furnished 1.55 g (81%) of the title compound as a light yellow solid. HRMS m/z calcd for C11H10ClN3 (M)+ 219.0563, found 219.0568. Anal. (C11H10ClN3) C, H, N.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. dissolutionThe yellow solid residue was dissolved in a small volume of methanol
  4. custompurified by silica gel chromatography (18×4 cm)
  5. customA second purification (SiO2; 16×4 cm)

Sources & evidence

ORD record
ord-af79e439855147d293293ba4dc476eba
Source dataset
uspto-grants-2007_07
Patent number
US07247633B2

Reaction notes

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