Tetrahydrofuran → 3-Chloro-6-hydrazinyl-4-(trimethylsilyl)pyridazine

HRID 2306592Notes

Reaction equation

HRID 2306592 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5]([Cl:12])=[CH:6][C:7]=1[Si:8]([CH3:11])([CH3:10])[CH3:9].[NH2:13][NH2:14].C1COCC1.C(N(CC)C(C)C)(C)C>>[Cl:12][C:5]1[N:4]=[N:3][C:2]([NH:13][NH2:14])=[C:7]([Si:8]([CH3:11])([CH3:10])[CH3:9])[CH:6]=1.[Cl:1][C:2]1[N:3]=[N:4][C:5]([NH:13][NH2:14])=[CH:6][C:7]=1[Si:8]([CH3:11])([CH3:10])[CH3:9]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 9321HydrazineHCID 81531DiisopropylethylamineHCID 151416463,6-Dichloro-4-(trimethylsilyl)pyridazine

Product 2

HCID 154861653-Chloro-6-hydrazinyl-4-(trimethylsilyl)pyridazineYield 67%HCID 154861826-Chloro-3-hydrazino-4-(trimethylsilyl)pyridazineYield 13%

Procedure

To a solution of 3,6-dichloro-4-(trimethylsilyl)pyridazine (9.67 g, 43.7 mmol) (Turck et al., J. Heterocycl. Chem., 1990, 27, 1377; prepared using the method described by Trécourt et al., J. Heterocycl. Chem., 1995, 32, 1057) in a 1.0 M solution of hydrazine in THF (131 ml, 131 mmol) was added N,N-diisopropylethylamine (7.5 ml, 43.8 mmol) and the mixture was stirred at reflux under nitrogen for 68 h. The mixture was allowed to cool, silica gel was added and the solvent was evaporated in vacuo. The residue was then purified by flash chromatography (silica gel, 5% MeOH/CH2Cl2) to give 1.24 g (13%) of 6-chloro-3-hydrazino-4-(trimethylsilyl)pyridazine and 6.34 g (67%) of the title compound as a yellow-brown solid; 1H NMR (360 MHz, CDCl3) δ 0.39 (9H, s), 3.96 (2H, br s), 6.24 (1H, br s), 7.08 (1H, s).

Workup

  1. customprepared
  2. temperatureat reflux under nitrogen for 68 h
  3. temperatureto cool
  4. additionsilica gel was added
  5. customthe solvent was evaporated in vacuo
  6. customThe residue was then purified by flash chromatography (silica gel, 5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-af457e95fb6347c9860d0527401746e0
Source dataset
uspto-grants-2004_12
Patent number
US06828322B2

Reaction notes

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