Ethyl Acetate → HCID 22724095, compound

HRID 2086766Notes

Reaction equation

HRID 2086766 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].Cl[C:13]1[N:18]=[CH:17][CH:16]=[CH:15][N:14]=1.C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CS(C)=O.O>[N:14]1[CH:15]=[CH:16][CH:17]=[N:18][C:13]=1[O:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 744042-ChloropyrimidineHCID 88068Methyl 3-Hydroxybenzoate

Product 1

HCID 22724095HCID 22724095, compoundYield 79.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of methyl 3-hydroxybenzoate (3.4 g), 2-chloropyrimidine (2.29 g) and potassium carbonate (3.04 g) in dimethylsulfoxide (30 ml) was stirred at 150° C. for 1 hour. The mixture was poured into a mixture of ethyl acetate and water. The organic phase was washed with water and brine, dried over magnesium sulfate and concentrated. The resultant solid was collected and washed with isopropyl ether to give methyl 3-(pyrimidine-2-yl)oxybenzoate (3.66 g).

Workup

  1. washThe organic phase was washed with water and brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe resultant solid was collected
  5. washwashed with isopropyl ether

Sources & evidence

ORD record
ord-312f6c57fe7746709ad8c56ed70a3d72
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

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