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

HRID 1179869Notes

Reaction equation

HRID 1179869 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-66924bfad4494248adde751c260b402a
Source dataset
uspto-grants-2007_10
Patent number
US07279470B2

Reaction notes

Loading…