Dimethylformamide dimethyl acetal → 3-(4-Chloro-2-methoxyphenyl)-1-methyl-6-trifluoromethyluracil

HRID 1271731Notes

Reaction equation

HRID 1271731 reaction equation
N[C:2]1[C:7](OC)=[C:6]([Cl:10])[CH:5]=[C:4](F)[C:3]=1[N:12]1[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[N:14]([CH3:23])[C:13]1=[O:24].[CH3:25][O:26]C(OC)N(C)C>>[Cl:10][C:6]1[CH:5]=[CH:4][C:3]([N:12]2[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:20])([F:21])[F:22])[N:14]([CH3:23])[C:13]2=[O:24])=[C:2]([O:26][CH3:25])[CH:7]=1

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 183145373-(2-Amino-4-chloro-6fluoro-3-methoxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H, 3H)pyrimidinedione

Product 1

HCID 232891923-(4-Chloro-2-methoxyphenyl)-1-methyl-6-trifluoromethyluracilYield 47%

Procedure

A mixture of 3-(2-amino-4-chloro-6-fluoro-3-methoxyphenyl)-1-methyl-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione (0.5 g, 1.4 mmol) and dimethylformamide dimethylacetal (0.8 g, 7 mmol) was refluxed for 4 hr under a blanket of nitrogen. Excess reagent was removed in vacuo and product extracted with ether. Solvent was removed to afford a residue which was chromatographed on silica gel. Elution of the column with hexane-ethyl acetate (6:4) afforded the title compound (0.22 g).

Workup

  1. temperaturewas refluxed for 4 hr under a blanket of nitrogen
  2. customExcess reagent was removed in vacuo and product
  3. extractionextracted with ether
  4. customSolvent was removed
  5. customto afford a residue which
  6. customwas chromatographed on silica gel
  7. washElution of the column with hexane-ethyl acetate (6:4)

Sources & evidence

ORD record
ord-3f9b5054161b41d497cdbefae46103b4
Source dataset
uspto-grants-2007_04
Patent number
USRE039590E1

Reaction notes

Loading…