Allyl Alcohol → 6-Chloro-2-phenylmethoxy-4-(2-propenyloxy)pyrimidine

HRID 1449438Notes

Reaction equation

HRID 1449438 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:3]=1.[CH2:17]([OH:20])[CH:18]=[CH2:19].[H-].[Na+]>CN(C)C=O>[Cl:8][C:6]1[N:5]=[C:4]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:3]=[C:2]([O:20][CH2:17][CH:18]=[CH2:19])[CH:7]=1

Participants

5

Reactant 3

HCID 7858Allyl AlcoholHCID 24758Sodium hydrideHCID 196938984,6-Dichloro-2-(phenylmethoxy)pyrimidine

Product 1

HCID 196938826-Chloro-2-phenylmethoxy-4-(2-propenyloxy)pyrimidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4,6-Dichloro-2-(phenylmethoxy)pyrimidine (Compound I-173) (1.5 g, 5.9 mmol) and allyl alcohol (0.342 g, 5.9×1.0 mmol) were introduced into a 50 ml eggplant type flask, to which dimethylformamide (20 ml) was added to form a solution. While cooling with ice, 60% sodium hydride (0.247 g, 5.9×1.05 mmol) which had been washed with hexane was added. After stirred for one night at room temperature, the reaction solution was poured into iced water and extracted with toluene (40 ml). The organic phase was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and thereafter, the solvent was distilled off to afford an oily product, which was then purified on silica gel column chromatography (Wakogel C300, 300 ml, hexane/ethyl acetate=25/1000(v/v)) to obtain the compound (I-343).

Workup

  1. additionwas added
  2. customto form a solution
  3. washhad been washed with hexane
  4. additionwas added
  5. additionthe reaction solution was poured into iced water
  6. extractionextracted with toluene (40 ml)
  7. washThe organic phase was washed with saturated aqueous sodium chloride
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationthe solvent was distilled off
  10. customto afford an oily product, which
  11. customwas then purified on silica gel column chromatography (Wakogel C300, 300 ml, hexane/ethyl acetate=25/1000(v/v))
  12. customto obtain the compound (I-343)

Sources & evidence

ORD record
ord-3266352ec5474fa5bf2757fac2b8a492
Source dataset
uspto-grants-1997_02
Patent number
US05599770

Reaction notes

Loading…