Lawesson's reagent → HCID 22142583, compound

HRID 2297178Notes

Reaction equation

HRID 2297178 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][NH:11][C:12]2[N:17]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=3[Cl:25])[C:15]([NH:26][C:27](=O)[CH3:28])=[CH:14][N:13]=2)[CH:5]=[CH:4][C:3]=1[N+:30]([O-:32])=[O:31].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:42])=CC=1>COCCOC>[NH2:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][NH:11][C:12]2[N:17]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=3[Cl:25])[C:15]([NH:26][C:27](=[S:42])[CH3:28])=[CH:14][N:13]=2)[CH:5]=[CH:4][C:3]=1[N+:30]([O-:32])=[O:31]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 22142528N-[2-({2-[(6-amino-5-nitro(2-pyridyl))amino]ethyl}amino)-4-(2,4-dichlorophenyl)pyrimidin-5-yl]acetamide

Product 1

HCID 22142583HCID 22142583, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

1 mmol of N-[2-({2-[(6-amino-5-nitro(2-pyridyl))amino]ethyl}amino)-4-(2,4-dichlorophenyl)pyrimidin-5-yl]acetamide and 2 mmol of Lawesson's reagent were stirred in 2 ml of DME at 80° C. The reaction mixture was concentrated in vacuo and diluted with water and ethyl acetate. The solution was extracted three times with ethyl acetate, dried over sodium sulfate, and purified by column chromatography eluting with 5-10% methanol/methylene chloride to obtain 1-{[2-({2-[(6-amino-5-nitro(2-pyridyl))-amino]ethyl}amino)-4-(2,4-dichlorophenyl)pyrimidin-5-yl]amino}ethane-1-thione.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additiondiluted with water and ethyl acetate
  3. extractionThe solution was extracted three times with ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. custompurified by column chromatography
  6. washeluting with 5-10% methanol/methylene chloride

Sources & evidence

ORD record
ord-ac09137ff67a4651a846473e640f461b
Source dataset
uspto-grants-2002_12
Patent number
US06489344B1

Reaction notes

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