N,N-Dimethylaniline → HCID 86626632, compound

HRID 556380Notes

Reaction equation

HRID 556380 reaction equation
O[C:2]1[N:7]=[CH:6][N:5]=[C:4]([CH2:8][O:9][C:10](=[O:16])[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH:3]=1.CN(C)C1C=CC=CC=1.O=P(Cl)(Cl)[Cl:28]>[N+](CC)(CC)(CC)CC.[Cl-].C(#N)C>[Cl:28][C:2]1[N:7]=[CH:6][N:5]=[C:4]([CH2:8][O:9][C:10](=[O:16])[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])[CH:3]=1

Participants

6

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 178445463HCID 178445463, compound

Product 1

HCID 86626632HCID 86626632, compound

Reagents, catalysts & solvents 2

HCID 5946Tetraethylammonium ChlorideCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 915 mg (4.08 mMol) hexanoic acid 6-hydroxy-pyrimidin-4-ylmethyl ester, 1.48 g (8.98 mMol) Et4NCl and 698 μl (5.44 mMol) N,N-dimethylaniline in 30 ml of acetonitrile, 3.73 ml (40.8 mMol) POCl3 are added. After stirring for 1 h at 60° C., the cooled solution is concentrated in vacuo. The residue is re-dissolved in EtOAc and water, the aq. layer separated off and extracted twice with EtOAc. The organic phases are washed with water, sat. NaHCO3 and brine, dried (Na2SO4) and concentrated, yielding the title compound as an oil: MS: [M+1]+=243/245; TLC(CH2Cl2): Rf=0.20.

Workup

  1. concentrationthe cooled solution is concentrated in vacuo
  2. dissolutionThe residue is re-dissolved in EtOAc
  3. customwater, the aq. layer separated off
  4. extractionextracted twice with EtOAc
  5. washThe organic phases are washed with water, sat. NaHCO3 and brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-db19999c6d38411a915a0aa4b35afa3b
Source dataset
uspto-grants-2011_11
Patent number
US08058276B2

Reaction notes

Loading…