N,N-Dimethylaniline → HCID 86626631, compound

HRID 556377Notes

Reaction equation

HRID 556377 reaction equation
O[C:2]1[CH: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])[N: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[CH: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])[N:3]=1

Participants

6

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 178445464HCID 178445464, compound

Product 1

HCID 86626631HCID 86626631, compound

Reagents, catalysts & solvents 2

HCID 5946Tetraethylammonium ChlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

To a solution of 300 mg (1.33 mMol) hexanoic acid 4-hydroxy-pyrimidin-2-ylmethyl ester, 487 mg (2.94 mMol) Et4NCl and 373 μl (2.94 mMol) N,N-dimethylaniline in 15 ml of acetonitrile, 1.22 ml (13.3 mMol) POCl3 are added. After stirring for 24 h at rt, the solution is concentrated in vacuo. The residue is re-dissolved in EtOAc and sat. NaHCO3, the aq. layer separated off and extracted twice with EtOAc. The organic phases are dried (Na2SO4) and concentrated. Chromatography (Combi Flash; hexane/ether 199:1→9:1→3:2) gives the title compound as an oil: MS: [M+1]+=243/245; TLC(CH2Cl2): Rf=0.26.

Workup

  1. concentrationthe solution is concentrated in vacuo
  2. dissolutionThe residue is re-dissolved in EtOAc
  3. customsat. NaHCO3, the aq. layer separated off
  4. extractionextracted twice with EtOAc
  5. dry with materialThe organic phases are dried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5f831aba77c9422281578662e969a249
Source dataset
uspto-grants-2011_11
Patent number
US08058276B2

Reaction notes

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