Thionyl Chloride → 5-(Chloromethyl)-2-phenylpyrimidine

HRID 914476Notes

Reaction equation

HRID 914476 reaction equation
[C:1]1([C:7]2[N:12]=[CH:11][C:10]([CH2:13]O)=[CH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:17])=O.C(=O)([O-])O.[Na+]>ClCCl>[Cl:17][CH2:13][C:10]1[CH:9]=[N:8][C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[N:12][CH:11]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 21298145(2-Phenylpyrimidin-5-yl)methanol

Product 1

HCID 242297265-(Chloromethyl)-2-phenylpyrimidineYield 95.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(2-Phenylpyrimidin-5-yl)methanol (1.75 g) synthesized in Reference Example 30 was dissolved in dichloromethane (20 mL) and, after ice-cooling, thionyl chloride (1.45 g) was added thereto, and the mixture was stirred at 0° C. for 2 hr. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the mixture was extracted with dichloromethane. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=2:1) to give the title compound (1.83 g) as a white solid.

Workup

  1. temperatureafter ice-cooling
  2. extractionthe mixture was extracted with dichloromethane
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel chromatography (elution solvent; hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-2a2408f3a59a41819f786668a1f80b55
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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