Triethylamine → Methyl-phenyl-carbamic Acid pyrimidin-2-yl Ester

HRID 1831225Notes

Reaction equation

HRID 1831225 reaction equation
Cl.[OH:2][C:3]1[N:8]=[CH:7][CH:6]=[CH:5][N:4]=1.[I-].C[N+]1C=CN([C:16](=[O:25])[N:17]([CH3:24])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)C=1.C(N(CC)CC)C>C(#N)C>[N:4]1[CH:5]=[CH:6][CH:7]=[N:8][C:3]=1[O:2][C:16](=[O:25])[N:17]([CH3:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 109478841-methyl-3-(methyl-phenyl-carbamoyl)-3H-imidazol-1-ium iodideHCID 178479648HCID 178479648, compound

Product 1

HCID 69518913Methyl-phenyl-carbamic Acid pyrimidin-2-yl EsterYield 12%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2-hydroxypyrimidine hydrochloride (0.40 g, 3.00 mmol), 1-methyl-3-(methyl-phenyl-carbamoyl)-3H-imidazol-1-ium iodide (1.03 g, 3.00 mmol) and triethylamine (0.83 ml, 6.00 mmol) in acetonitrile (15 ml) was stirred at room temperature overnight. The solvent was evaporated in vacuo and the residue was purified by flash column chromatography (SiO2, ethyl acetate) followed by crystallisation from ethyl acetate:heptane yielding the title compound (0.08 g, 12% 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)
  3. customfollowed by crystallisation from ethyl acetate

Sources & evidence

ORD record
ord-90610637fddf451ebf9dae00a3263678
Source dataset
uspto-grants-2006_06
Patent number
US07067517B2

Reaction notes

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