HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 892991
Notes
Print preview

Reaction equation

HRID 892991 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 702
Ethanol
Solvent
2×

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-305847ff7d8f4b249024227bdbf9b9df
Source dataset
uspto-grants-1992_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05120843

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes