Methyl p-toluenesulfonate → HCID 86616753, compound

HRID 2243776Notes

Reaction equation

HRID 2243776 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]([CH2:9][CH2:10][OH:11])[C:4](=[O:12])[N:3]=1.[C:13]1([CH3:24])[CH:18]=[CH:17][C:16]([S:19]([O:22]C)(=[O:21])=[O:20])=[CH:15][CH:14]=1>C(#N)C>[C:13]1([CH3:24])[CH:14]=[CH:15][C:16]([S:19]([O-:22])(=[O:20])=[O:21])=[CH:17][CH:18]=1.[OH:11][CH2:10][CH2:9][NH+:5]1[C:6]([CH3:8])=[CH:7][CH:2]([CH3:1])[N:3]([CH3:13])[C:4]1=[O:12]

Participants

4

Reactant 2

HCID 6645Methyl p-toluenesulfonateHCID 1219311-(2-Hydroxyethyl)-4,6-dimethylpyrimidin-2(1H)-one

Product 1

HCID 86616753HCID 86616753, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

Under a protective-gas atmosphere, a mixture of 9.2 g (0.055 mol) of 4,6-dimethyl-1-(2-hydroxyethyl)pyrimidin-2(1H)-one and 13.1 g (0.068 mol) of methyl p-toluenesulfonate in 700 ml of acetonitrile was heated under reflux for 12 hours. After cooling, about ⅔ of the solvent was removed on a rotary evaporator, the remaining residue was mixed with the same amount of diethyl ether and cooled to 0° C. At low temperature, firstly an oil separated off, which crystallized out after some time. The crystalline product was filtered off.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 12 hours
  3. temperatureAfter cooling, about ⅔ of the solvent
  4. customwas removed on a rotary evaporator
  5. additionthe remaining residue was mixed with the same amount of diethyl ether
  6. customAt low temperature, firstly an oil separated off
  7. customwhich crystallized out after some time
  8. filtrationThe crystalline product was filtered off

Sources & evidence

ORD record
ord-fdcbdba07d8c45e29f3e7e93261f45b5
Source dataset
uspto-grants-2010_03
Patent number
US07678156B2

Reaction notes

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