Triethylamine → 2-chloro-6-(4-methylpiperazin-1-yl)pyrazine

HRID 879517Notes

Reaction equation

HRID 879517 reaction equation
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1.[CH3:9][N:10]1[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.C(N(CC)CC)C>O1CCOCC1>[Cl:8][C:4]1[CH:5]=[N:6][CH:7]=[C:2]([N:13]2[CH2:14][CH2:15][N:10]([CH3:9])[CH2:11][CH2:12]2)[N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 785042,6-Dichloropyrazine

Product 1

HCID 99207702-chloro-6-(4-methylpiperazin-1-yl)pyrazine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To 2,6-dichloropyrazine (150 mg, 1.007 mmol) in 1,4-dioxane (1.0 mL) was added 1-methylpiperazine (121.0 mg, 0.13 mL, 1.208 mmol) followed by triethylamine (203.8 mg, 0.281 mL, 2.014 mmol). The reaction mixture was stirred at room temperature for 24 h then concentrated. Purification by flash column chromatography on silica gel using 100:5:1 EtOAc/MeOH/NH4OH (0 to 100%) in EtOAc provided the product. LCMS-ESI+ calc'd for C9H14ClN4 (M+H+): 213.1; Found: 213.2 (M+H+).

Workup

  1. concentrationthen concentrated
  2. customPurification by flash column chromatography on silica gel using 100:5:1 EtOAc/MeOH/NH4OH (0 to 100%) in EtOAc
  3. customprovided the product

Sources & evidence

ORD record
ord-27a5dd716bc84292b868fb939f072276
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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