Triethylamine → Methyl-phenyl-carbamic Acid 4,6-dimethyl-pyrimidin-2-yl Ester

HRID 1831232Notes

Reaction equation

HRID 1831232 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([OH:9])[N:3]=1.[I-].C[N+]1C=CN([C:17](=[O:26])[N:18]([CH3:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)C=1.C(N(CC)CC)C>C(#N)C>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([O:9][C:17](=[O:26])[N:18]([CH3:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 95084,6-Dimethylpyrimidin-2-olHCID 109478841-methyl-3-(methyl-phenyl-carbamoyl)-3H-imidazol-1-ium iodide

Product 1

HCID 69519301Methyl-phenyl-carbamic Acid 4,6-dimethyl-pyrimidin-2-yl EsterYield 60%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4,6-dimethyl-2-hydroxypyrimidine (0.37 g, 3.00 mmol) ), 1-methyl-3-(methyl-phenyl-carbamoyl)-3H-imidazol-1-ium iodide (1.03 g, 3.00 mmol) and triethylamine (0.42 ml, 3.00 mmol) in acetonitrile (15 ml) was stirred at room temperature for 18 hours. The solvent was evaporated in vacuo and the residue was purified by flash column chromatography (SiO2, ethyl acetate:heptane (50:50)) yielding the title compound (0.46 g, 60% yield) as a white solid.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was purified by flash column chromatography (SiO2, ethyl acetate:heptane (50:50))

Sources & evidence

ORD record
ord-c49d3cb21fcc4270a0c1182f0045ade4
Source dataset
uspto-grants-2006_06
Patent number
US07067517B2

Reaction notes

Loading…