Sodium Hydroxide → HCID 18546790, compound

HRID 1634906Notes

Reaction equation

HRID 1634906 reaction equation
O[CH2:2][C:3]1[CH:8]=[C:7]([C:9]2[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH3:18])=[C:11]([O:19][CH3:20])[CH:10]=2)[N:6]=[CH:5][N:4]=1.S(Cl)([Cl:23])=O.[OH-].[Na+]>ClCCl>[Cl:23][CH2:2][C:3]1[CH:8]=[C:7]([C:9]2[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH3:18])=[C:11]([O:19][CH3:20])[CH:10]=2)[N:6]=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 18546814HCID 18546814, compound

Product 1

HCID 18546790HCID 18546790, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Hydroxymethyl-6-(3,4,5-trimethoxyphenyl)-pyrimidine (339 mg) was dissolved in dichloromethane (20 mL), and to the solution thionyl chloride (0.15 mL) was added dropwise under ice cooling, and the mixture was stirred for 1 hour. An aqueous solution of sodium hydroxide was added to the reaction mixture to neutralize it, and extraction was conducted with methylene chloride. The resultant organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1) to obtain the title compound.

Workup

  1. extractionit, and extraction
  2. washThe resultant organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-a2677bb299cb4e47befbe367a7384322
Source dataset
uspto-grants-2003_01
Patent number
US06509329B1

Reaction notes

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