1,4-Dioxane → HCID 20339592, compound

HRID 1395547Notes

Reaction equation

HRID 1395547 reaction equation
C([Li])CCC.O1CCOCC1.[CH3:12][N:13]([CH3:24])[C:14]([NH:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([NH2:23])[N:18]=1)=[O:15].Cl.[CH:26]([N:29]([CH:33]([CH3:35])[CH3:34])[CH2:30][CH2:31]Cl)([CH3:28])[CH3:27]>CCCCCC.C(O)C>[CH3:12][N:13]([CH3:24])[C:14]([N:16]([CH2:31][CH2:30][N:29]([CH:33]([CH3:35])[CH3:34])[CH:26]([CH3:28])[CH3:27])[C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([NH2:23])[N:18]=1)=[O:15]

Participants

7

Reactant 4

HCID 312751,4-DioxaneHCID 779422-Chloroethyldiisopropylammonium chlorideHCID 20339614N'-(6-Aminopyridin-2-yl)-N,N-dimethylureaHCID 178418339Butyllithium2×

Product 1

HCID 20339592HCID 20339592, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8058HexaneSolvent

Conditions

Temperature
-25 °C

Procedure

Under a nitrogen atmosphere, n-butyl lithium solution (15.5 ml., 0.025 mole) is added dropwise with stirring to a dioxane (50 ml.) solution of N,N-dimethyl-N'-(6-amino-2-pyridyl)urea (4.5 g., 0.025 mole) at 10° C. Then 2-diisopropylaminoethyl chloride hydrochloride (55.5 g., 0.275 mole) is added followed by another portion of n-butyl lithium (15.5 ml., 0.025 mole). The mixture is heated at reflux over night. Ethanol (30 ml.) is added with cooling and the mixture is filtered and concentrated in vacuo. The residue is treated with ether and is filtered to remove salts. Removal of the ether in vacuo gives 5.1 g. of viscous oil. The crude oil is taken up in hexane, filtered and cooled to -25° C. Filtration gives 1.5 g. of white solid, m.p. 86°-88° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux over night
  3. temperaturewith cooling
  4. filtrationthe mixture is filtered
  5. concentrationconcentrated in vacuo
  6. additionThe residue is treated with ether
  7. filtrationis filtered
  8. customto remove salts
  9. customRemoval of the ether in vacuo
  10. customgives 5.1 g
  11. filtrationfiltered
  12. filtrationFiltration
  13. customgives 1.5 g

Sources & evidence

ORD record
ord-a3ac5a4c45e9474296969eb4ceb613ae
Source dataset
uspto-grants-1980_05
Patent number
US04203988

Reaction notes

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