N,N-Dimethylaniline → Methyl [4-chloro-2-(4-nitrobenzyl)pyrimidin-5-yl]acetate

HRID 2353322Notes

Reaction equation

HRID 2353322 reaction equation
O[C:2]1[C:7]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:6][N:5]=[C:4]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)[N:3]=1.P(Cl)(Cl)([Cl:25])=O.CN(C)C1C=CC=CC=1>>[Cl:25][C:2]1[C:7]([CH2:8][C:9]([O:11][CH3:12])=[O:10])=[CH:6][N:5]=[C:4]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)[N:3]=1

Participants

4

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 178499546HCID 178499546, compound

Product 1

HCID 57542076Methyl [4-chloro-2-(4-nitrobenzyl)pyrimidin-5-yl]acetateYield 64%

Conditions

Temperature
150 °C

Procedure

A mixture of methyl [4-hydroxy-2-(4-nitrobenzyl)pyrimidin-5-yl]acetate (4.0 g, 13.19 mmol), phosphorus oxychloride (6.15 mL, 65.95 mmol) and N,N-dimethylaniline (2.51 mL, 19.78 mmol) was stirred at 150° C. for 3 hours. After the removal of the excess phosphorus oxychloride, the residue was dissolved with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by column chromatography on silica-gel, (hexane:ethyl acetate, 7/3) to give methyl [4-chloro-2-(4-nitrobenzyl)pyrimidin-5-yl]acetate (2.70 g, 64%) as orange solid.

Workup

  1. customAfter the removal of the excess phosphorus oxychloride
  2. dissolutionthe residue was dissolved with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by column chromatography on silica-gel, (hexane:ethyl acetate, 7/3)

Sources & evidence

ORD record
ord-d1a6e0b6f93b49e1be2f1038064aa0f5
Source dataset
uspto-grants-2010_07
Patent number
US07750014B2

Reaction notes

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