Diphosgene → Methyl-m-tolyl-carbamic Acid 4-trifluoromethyl-pyrimidin-2-yl Ester

HRID 1831245Notes

Reaction equation

HRID 1831245 reaction equation
[O:1]=[C:2](Cl)[O:3][C:4](Cl)(Cl)Cl.[F:9][C:10]([F:19])([F:18])[C:11]1[CH:16]=[CH:15][N:14]=C(O)[N:12]=1.[CH3:20][NH:21][C:22]1[CH:23]=[C:24]([CH3:28])[CH:25]=[CH:26][CH:27]=1>O1CCCC1>[F:9][C:10]([F:19])([F:18])[C:11]1[CH:16]=[CH:15][N:14]=[C:4]([O:3][C:2](=[O:1])[N:21]([CH3:20])[C:22]2[CH:23]=[C:24]([CH3:28])[CH:25]=[CH:26][CH:27]=2)[N:12]=1

Participants

5

Reactant 3

HCID 10426DiphosgeneHCID 69675Benzenamine, N,3-dimethyl-HCID 178517744HCID 178517744, compound

Product 1

HCID 69518844Methyl-m-tolyl-carbamic Acid 4-trifluoromethyl-pyrimidin-2-yl EsterYield 7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At 0° C. diphosgene (0.99 g, 5.00 mmol) was added to a stirred solution of 4-trifluoromethyl-2-hydroxypyrimidine (1.64 g, 10.0 mmol) in tetrahydrofuran (25 ml). The cooling bath was removed and stirring was continued at room temperature for 1 hour. Methyl-m-tolyl-amine (0.30 g, 2.50 mmol) was added to one-fourth of the solution. After stirring overnight at room temperature the solvent was evaporated in vacuo and the residue was purified by flash column chromatography (SiO2, ethyl acetate:heptane (20:80)) followed by preparative HPLC, yielding the title compound (51 mg, 7%) as a colourless oil.

Workup

  1. customThe cooling bath was removed
  2. stirringAfter stirring overnight at room temperature the solvent
  3. customwas evaporated in vacuo
  4. customthe residue was purified by flash column chromatography (SiO2, ethyl acetate:heptane (20:80))

Sources & evidence

ORD record
ord-e774d3ce10ce4f268edf7fdb83ea7719
Source dataset
uspto-grants-2006_06
Patent number
US07067517B2

Reaction notes

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