Dimethyl Sulfoxide → Methyl 4'-methyl-5-(pyrimidin-2-yloxy)biphenyl-3-carboxylate

HRID 1845264Notes

Reaction equation

HRID 1845264 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:15]([O:17][CH3:18])=[O:16])[CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][CH:9]=2)[CH:7]=1.[H-].[Na+].CS(C)=O.Cl[C:26]1[N:31]=[CH:30][CH:29]=[CH:28][N:27]=1>O1CCCC1>[CH3:14][C:11]1[CH:10]=[CH:9][C:8]([C:6]2[CH:7]=[C:2]([O:1][C:26]3[N:31]=[CH:30][CH:29]=[CH:28][N:27]=3)[CH:3]=[C:4]([C:15]([O:17][CH3:18])=[O:16])[CH:5]=2)=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 744042-ChloropyrimidineHCID 58187967Methyl 5-hydroxy-4'-methyl-[1,1'-biphenyl]-3-carboxylate

Product 1

HCID 58188218Methyl 4'-methyl-5-(pyrimidin-2-yloxy)biphenyl-3-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 5-hydroxy-4′-methylbiphenyl-3-carboxylate (300 mg, 1.24 mmol) in tetrahydrofuran (20 mL) at 0° C. was added sodium hydride (60% in mineral oil, 55 mg, 1.37 mmol) over a period of 10 minutes. The reaction mixture was concentrated to afford a green solid. A microwave vial was charged with the resulting green solid, dimethyl sulfoxide (8 mL), and 2-chloropyrimidine (118 mg, 0.98 mmol). The mixture was subjected to microwave irradiation at 100° C. for 4 minutes. After cooling, the mixture was filtered through Celite and the filtrate was concentrated. The residue was purified by flash chromatography to afford the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto afford a green solid
  3. customirradiation at 100° C. for 4 minutes
  4. temperatureAfter cooling
  5. filtrationthe mixture was filtered through Celite
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-fbd4bb8346d246af815030e84b257bdd
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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