Lawesson's reagent → Ethyl 1-[(6-methyl-2,3'-bipyridin-5-yl)methyl]-4-thioxo-1,4-dihydropyrido[2,3-c]pyridazine-3-carboxylate

HRID 2067109Notes

Reaction equation

HRID 2067109 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[CH:5]=[CH:4][C:3]=1[CH2:14][N:15]1[C:20]2[N:21]=[CH:22][CH:23]=[CH:24][C:19]=2[C:18](=O)[C:17]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[N:16]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:40])=CC=1>O1CCOCC1.C1(C)C=CC=CC=1>[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[CH:5]=[CH:4][C:3]=1[CH2:14][N:15]1[C:20]2[N:21]=[CH:22][CH:23]=[CH:24][C:19]=2[C:18](=[S:40])[C:17]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[N:16]1

Participants

5

Reactant 2

HCID 87949Lawesson's reagentHCID 66744617Ethyl 1-[(6-methyl-2,3'-bipyridin-5-yl)methyl]-4-oxo-1,4-dihydropyrido[2,3-c]pyridazine-3-carboxylate

Product 1

HCID 86662100Ethyl 1-[(6-methyl-2,3'-bipyridin-5-yl)methyl]-4-thioxo-1,4-dihydropyrido[2,3-c]pyridazine-3-carboxylate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Procedure

Ethyl 1-[(6-methyl-2,3′-bipyridin-5-yl)methyl]-4-oxo-1,4-dihydropyrido[2,3-c]pyridazine-3-carboxylate (139 mg, 0.346 mmol) was suspended in dioxane (6 mL) and toluene (3 mL), placed into a preheated oil bath at 100° C. and treated with Lawesson's Reagent (84.0 mg, 0.208 mmol, 0.6 equiv) portionwise over 5 minutes. After stirring for 30 minutes, the mixture was cooled to ambient temperature and concentrated in vacuo. The residue was purified by silica gel gradient chromatography (100:0 to 0:100; hexanes:ethyl acetate containing 5% methanol), providing the titled compound as brownish-green foam.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by silica gel gradient chromatography (100:0 to 0:100; hexanes:ethyl acetate containing 5% methanol)

Sources & evidence

ORD record
ord-62e60cd07e314da69612d09ce5f1f100
Source dataset
uspto-grants-2012_10
Patent number
US08293744B2

Reaction notes

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