Hexamethylphosphoramide → HCID 89498219, compound

HRID 1778855Notes

Reaction equation

HRID 1778855 reaction equation
[I:1][C:2]1[CH:3]=[N:4][N:5]([CH2:8][C:9]2([OH:15])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[C:6]=1[CH3:7].[H-].[Na+].Br[CH2:19][CH2:20][O:21][CH3:22].CN(C)P(N(C)C)(N(C)C)=O>O1CCCC1.C(OCC)(=O)C>[I:1][C:2]1[CH:3]=[N:4][N:5]([CH2:8][C:9]2([O:15][CH2:19][CH2:20][O:21][CH3:22])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]2)[C:6]=1[CH3:7]

Participants

7

Reactant 4

HCID 12679HexamethylphosphoramideHCID 24758Sodium hydride2×HCID 809722-Bromoethyl methyl etherHCID 89498419HCID 89498419, compound

Product 1

HCID 89498219HCID 89498219, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of EXAMPLE 101B (260 mg) in tetrahydrofuran (15 mL) was added NaH (97 mg). The mixture was stirred for 30 minutes. 1-Bromo-2-methoxyethane (564 mg) was added to the mixture and the mixture was stirred for 3 hours. The mixture was then stirred at reflux for 2 hours. Hexamethylphosphoramide (5 mL) and additional NaH (200 mg) were added to the mixture and the mixture was stirred at reflux overnight. The reaction mixture was diluted with ethyl acetate (200 mL) and washed with water and brine and dried over Na2SO4. The residue, after filtration and evaporation of the solvent, was loaded on a 40 g column and eluted with 20% ethyl acetate in hexane to give the title compound.

Workup

  1. stirringthe mixture was stirred for 3 hours
  2. stirringThe mixture was then stirred
  3. temperatureat reflux for 2 hours
  4. stirringthe mixture was stirred
  5. temperatureat reflux overnight
  6. washwashed with water and brine
  7. dry with materialdried over Na2SO4
  8. filtrationThe residue, after filtration and evaporation of the solvent
  9. washeluted with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-8c38d953ab5f4c0ea564b19b5aa90a22
Source dataset
uspto-grants-2016_02
Patent number
US09266877B2

Reaction notes

Loading…