Sodium hydride → HCID 53783840, compound

HRID 1193918Notes

Reaction equation

HRID 1193918 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]=[C:10]2[O:20][CH3:21])=[C:4]([F:22])[CH:3]=1.[H-].[Na+].FC(F)(F)S(O[CH2:31][CH2:32][O:33][N:34]=[C:35]([CH3:37])[CH3:36])(=O)=O>CN(C)C=O>[Cl:1][C:2]1[C:7]([O:8][CH2:31][CH2:32][O:33][N:34]=[C:35]([CH3:37])[CH3:36])=[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]=[C:10]2[O:20][CH3:21])=[C:4]([F:22])[CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 21270742HCID 21270742, compoundHCID 21270790HCID 21270790, compound

Product 1

HCID 53783840HCID 53783840, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.70 g of 1-(4-chloro-2-fluoro-5-hydroxyphenyl)-2-methoxy-4-trifluoromethyl-6(1H)-pyrimidinone are added at room temperature while stirring to a suspension of 0.22 g of a 55% sodium hydride dispersion in 25 ml of dimethylformamide and the mixture is stirred for 1 hour. Subsequently, the previously prepared solution of 2-[(isopropylideneamino)oxy]-ethyl trifluoromethanesulphonate is added at 0° C. and the mixture is stirred for 30 minutes. The reaction mixture is washed twice with 100 ml of water each time and the organic phase is dried over anhydrous sodium sulphate and evaporated to dryness under reduced pressure. The residue is purified by chromatography on a silica gel column using n-hexane/diethyl ether (2:1) as the eluent. The product is recrystallized from n-hexane/diethyl ether. There is obtained 1-[4-chloro-2-fluoro-5-{2-[(isopropylideneamino)oxy] -ethoxy} -phenyl]-2-methoxy-4-trifluoromethyl-6(1H)-pyrimidinone, m.p. 136°-138° C.

Workup

  1. stirringthe mixture is stirred for 30 minutes
  2. washThe reaction mixture is washed twice with 100 ml of water each time
  3. dry with materialthe organic phase is dried over anhydrous sodium sulphate
  4. customevaporated to dryness under reduced pressure
  5. customThe residue is purified by chromatography on a silica gel column
  6. customThe product is recrystallized from n-hexane/diethyl ether

Sources & evidence

ORD record
ord-aef7e68129ab4ed3a61770c461d018a3
Source dataset
uspto-grants-1989_03
Patent number
US04812164

Reaction notes

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