Hydrazine → 1-Formyl 4-[5,6-bis(2-pyridinyl)-1,2,4-triazin-3-yl]-piperazine

HRID 2372618Notes

Reaction equation

HRID 2372618 reaction equation
I.[CH:2]([N:4]1[CH2:9][CH2:8][N:7]([C:10](=[NH:12])[NH2:11])[CH2:6][CH2:5]1)=[O:3].[O-]CC.[Na+].[NH2:17]N.[CH:19]1[CH:24]=[C:23]([C:25]([C:27]([C:29]2[N:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=O)=O)[N:22]=[CH:21][CH:20]=1>C(O)C>[CH:2]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[N:11]=[N:17][C:27]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][N:34]=3)=[C:25]([C:23]3[CH:24]=[CH:19][CH:20]=[CH:21][N:22]=3)[N:12]=2)[CH2:6][CH2:5]1)=[O:3]

Participants

6

Reactant 4

HCID 9321HydrazineHCID 68115Di-2-pyridylethanedioneHCID 2723922Sodium ethoxideHCID 130363664-Formyl-piperazinecarboximidamide hydroiodide

Product 1

HCID 224187591-Formyl 4-[5,6-bis(2-pyridinyl)-1,2,4-triazin-3-yl]-piperazine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A mixture of 4-formyl-piperazinecarboximidamide hydroiodide (prepared according to U.S. Pat. No. 4,351,832) in ethanol (4 ml) and ethanolic sodium ethoxide (1.4N, 6.8 ml) is stirred for 15 min and then anhydrous hydrazine (0.32 g) in ethanol (3 ml) is added. The mixture is stirred an additional 15 min, then 2,2'-pyridil (2.12 g) is added. The mixture is stirred for 12 hours at 25° and concentrated. The residue is chromatographed on silica gel eluting with a methylene chloride/methanol mixture. The appropriate fractions are pooled and concentrated to give 1-formyl 4-[5,6-bis(2-pyridinyl)-1,2,4-triazin-3-yl]-piperazine. Hydrolysis of the formamide in the usual way (PREPARATION A-14) gives the title compound.

Workup

  1. customprepared
  2. stirringThe mixture is stirred for 12 hours at 25°
  3. concentrationconcentrated
  4. customThe residue is chromatographed on silica gel eluting with a methylene chloride/methanol mixture
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f409e917d0df4f388aac3762767e4df0
Source dataset
uspto-grants-1992_03
Patent number
US05099019

Reaction notes

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