Benzyl Alcohol → 4,6-Dichloro-2-(phenylmethoxy)pyrimidine

HRID 1449437Notes

Reaction equation

HRID 1449437 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl: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.CN(C)C=O.[H-].[Na+]>CCCCCC>[Cl:1][C:2]1[CH:7]=[C:6]([Cl: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 6228DimethylformamideHCID 24758Sodium hydrideHCID 2396854,6-Dichloro-2-(methylsulfonyl)pyrimidine

Product 1

HCID 196938984,6-Dichloro-2-(phenylmethoxy)pyrimidine

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

4, 6-Dichloro-2-(methysulfonyl)pyrimidine (Compound III-5) (21.3 g, 93.8 mmol) and benzyl alcohol (Compound II-64) (10.1 g, 93.8×1.0 mmol) were introduced into a 500 ml eggplant type flask, to which dimethylformamide (150 ml) was added to form a solution. While stirring in ice bath, 60% sodium hydride (3.94 g, 93.8×1.05 mmol) which had been washed with hexane was added. After bubbling was ceased, ice bath was removed and the reaction solution was stirred for 2 hours at room temperature. The reaction mixture was poured onto ice and the separated organic matter was extracted with ethyl acetate. The organic phase was washed successively with diluted hydrochloric acid and saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and thereafter, the solvent was distilled off. The residue was purified on silica gel column chromatography (Wakogel C300, ethyl acetate/hexane=1/50(v/v)) to obtain the compound (I-173) as an oily product.

Workup

  1. additionwas added
  2. customto form a solution
  3. additionwas added
  4. customAfter bubbling
  5. customice bath was removed
  6. stirringthe reaction solution was stirred for 2 hours at room temperature
  7. additionThe reaction mixture was poured onto ice
  8. extractionthe separated organic matter was extracted with ethyl acetate
  9. washThe organic phase was washed successively with diluted hydrochloric acid and saturated aqueous sodium chloride
  10. dry with materialdried over anhydrous sodium sulfate
  11. distillationthe solvent was distilled off
  12. customThe residue was purified on silica gel column chromatography (Wakogel C300, ethyl acetate/hexane=1/50(v/v))
  13. customto obtain the compound (I-173) as an oily product

Sources & evidence

ORD record
ord-3abc31af1b834680b083a08d7231d584
Source dataset
uspto-grants-1997_02
Patent number
US05599770

Reaction notes

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