Benzyl Alcohol → HCID 19693890, compound

HRID 1449436Notes

Reaction equation

HRID 1449436 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([Br:8])[N:5]=[C:4](S(C)(=O)=O)[N:3]=1.[CH2:13]([OH:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[H-].[Na+].O>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[C:6]([Br:8])[N:5]=[C:4]([O:20][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:3]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 24758Sodium hydrideHCID 196938884,6-Dibromo-2-(methanesulfonyl)pyrimidine

Product 1

HCID 19693890HCID 19693890, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

4,6-dibromo-2-(methysulfonyl)pyrimidine (Compound III-3) (1.5 g, 0.00476 mol) was dissolved in toluene, and benzyl alcohol (Compound II-64) (0.515 g, 0.00476×1.0 mol) was added thereto. While cooling with ice, 60% sodium hydride (0.21 g, 0.00476×1.1 mol) was added while stirring. After stirred for 6 hours, the reaction solution was poured into water and extracted with toluene. The organic phase was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate and filtered, and thereafter, the solvent was distilled off. The residue was purified on silica gel column chromatography (Wakogel C300, 100 ml, ethyl acetate/hexane=20 ml/400 ml) to obtain the compound (I-81) as an oily product from the fraction of 100 ml to 120 ml.

Workup

  1. additionwas added
  2. stirringAfter stirred for 6 hours
  3. extractionextracted with toluene
  4. washThe organic phase was washed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. distillationthe solvent was distilled off
  8. customThe residue was purified on silica gel column chromatography (Wakogel C300, 100 ml, ethyl acetate/hexane=20 ml/400 ml)
  9. customto obtain the compound (I-81) as an oily product from the fraction of 100 ml to 120 ml

Sources & evidence

ORD record
ord-e1f632bfd538433ab83a86d64fc8e5d3
Source dataset
uspto-grants-1997_02
Patent number
US05599770

Reaction notes

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