2,5-Dimethoxytetrahydrofuran → HCID 20032934, compound

HRID 231476Notes

Reaction equation

HRID 231476 reaction equation
[CH3:1][CH:2]1[C:7]([C:8]2[CH:9]=[CH:10][C:11]([NH2:14])=[N:12][CH:13]=2)=[N:6][NH:5][C:4](=[O:15])[CH2:3]1.CO[CH:18]1[CH2:22][CH2:21][CH:20](OC)O1>C(O)(=O)C>[CH3:1][CH:2]1[C:7]([C:8]2[CH:9]=[CH:10][C:11]([N:14]3[CH:18]=[CH:22][CH:21]=[CH:20]3)=[N:12][CH:13]=2)=[N:6][NH:5][C:4](=[O:15])[CH2:3]1

Participants

4

Reactant 2

HCID 790982,5-DimethoxytetrahydrofuranHCID 20032965HCID 20032965, compound

Product 1

HCID 20032934HCID 20032934, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1.0 g. (5 mmole) 4,5-dihydro-5-methyl-6-(2-amino-5-pyridyl)-3(2H)-pyridazinone, 0.66 g. (5 mmole) 2,5-dimethoxytetrahydrofuran and 15 ml. acetic acid was heated under reflux for 30 minutes. The reaction mixture was evaporated, the residue was taken up in dichloromethane, washes with an aqueous solution of sodium hydrogen carbonate, evaporated and the residue chromatographed on silica gel (elution agent: trichloromethane/methanol 19:1 v/v). There were obained 0.5 g. of the title compound (39% of theory); m.p. 192°-193° C., after recrystallisation from diethyl ether.

Workup

  1. additionA mixture of 1.0 g
  2. temperatureunder reflux for 30 minutes
  3. customThe reaction mixture was evaporated
  4. customwashes with an aqueous solution of sodium hydrogen carbonate, evaporated
  5. customthe residue chromatographed on silica gel (elution agent: trichloromethane/methanol 19:1 v/v)
  6. customm.p. 192°-193° C., after recrystallisation from diethyl ether

Sources & evidence

ORD record
ord-69136d51e93b4c84a69409c0d7da8572
Source dataset
uspto-grants-1989_07
Patent number
US04847251

Reaction notes

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