Chloromethyl Methyl Ether → HCID 20025942, compound

HRID 1722957Notes

Reaction equation

HRID 1722957 reaction equation
[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([N:9]2[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[N:11]([CH3:20])[C:10]2=[O:21])=[C:4]([F:22])[CH:3]=1.[H-].[Na+].[H][H].[CH3:27][O:28][CH2:29]Cl>CN(C)C=O>[Cl:1][C:2]1[C:7]([O:8][CH2:27][O:28][CH3:29])=[CH:6][C:5]([N:9]2[C:14](=[O:15])[CH:13]=[C:12]([C:16]([F:18])([F:17])[F:19])[N:11]([CH3:20])[C:10]2=[O:21])=[C:4]([F:22])[CH:3]=1

Participants

6

Reactant 4

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 112677571-methyl-6-trifluoromethyl-3-(4-chloro-2-fluoro-5-hydroxyphenyl)-2,4(1H,3H)-pyrimidinedioneHCID 178418361HCID 178418361, compound

Product 1

HCID 20025942HCID 20025942, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 2.00 g of 3-(4-chloro-2-fluoro-5-hydroxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione in 20 ml of dimethylformamide is added to a suspension of 0.26 g of a 55% sodium hydride dispersion in 20 ml of absolute dimethylformamide and the mixture is stirred at room temperature until the hydrogen evolution has finished. Subsequently, 0.57 g of chlorodimethyl ether is added and the mixture is stirred at room temperature for 2 hours. The reaction mixture is evaporated to dryness under reduced pressure, the residue is taken up in 100 ml of ethyl acetate and the solution is washed twice with water, dried over anhydrous sodium sulphate and evaporated to dryness under reduced pressure. The residue is purified by chromatography on a silica gel column using diethyl ether/n-hexane as the eluent. There is obtained 3-(4-chloro-2-fluoro-5 -methoxymethoxy-phenyl)-1-methyl-6-trifluoromethyl -2,4(1H,3H)-pyrimidinedione, 1H-NMR (CDCl3, 400 MHz): 7.31 ppm (d,1H), 7.12 ppm (d,1H), 6.36 ppm (s,1H), 5.22 ppm (d,1H), 5.19 ppm (d,1H), 3.55 ppm (d,3H), 3.51 ppm (s,3H).

Workup

  1. customThe reaction mixture is evaporated to dryness under reduced pressure
  2. washthe solution is washed twice with water
  3. dry with materialdried over anhydrous sodium sulphate
  4. customevaporated to dryness under reduced pressure
  5. customThe residue is purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-b67e0faf5a604f8e84b3999ca6de22f2
Source dataset
uspto-grants-1989_08
Patent number
US04859229

Reaction notes

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