Bromine → 5-Bromo-1-{[2-fluoro-6-(trifluoromethyl)phenyl]methyl}-6-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

HRID 28494Notes

Reaction equation

HRID 28494 reaction equation
[Br:1]Br.[F:3][C:4]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[C:5]=1[CH2:6][N:7]1[C:12]([CH3:13])=[CH:11][C:10](=[O:14])[NH:9][C:8]1=[O:15]>C(O)(=O)C>[Br:1][C:11]1[C:10](=[O:14])[NH:9][C:8](=[O:15])[N:7]([CH2:6][C:5]2[C:16]([C:20]([F:23])([F:21])[F:22])=[CH:17][CH:18]=[CH:19][C:4]=2[F:3])[C:12]=1[CH3:13]

Participants

4

Reactant 2

HCID 24408BromineHCID 220378661-[[2-Fluoro-6-(trifluoromethyl)phenyl]methyl]-6-methylpyrimidine-2,4-dione

Product 1

HCID 116823865-Bromo-1-{[2-fluoro-6-(trifluoromethyl)phenyl]methyl}-6-methyl-1,2,3,4-tetrahydropyrimidine-2,4-dioneYield 48,750%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Bromine (16.5 mL, 0.32 mmol) was added to 1-[2-fluoro-6-(trifluoromethyl)benzyl]-6-methylpyrimidine-2-4(1H-3H)-dione 1c (48.5 g, 0.16 mol) in 145 mL of acetic acid. The resulting mixture became clear then formed precipitate within an hour. After 2 hours stirring, the yellow solid was filtered and washed with cold EtOAc to an almost white solid. The filtrate was washed with sat. NaHCO3 and dried over Na2SO4. Evaporation gave a yellow solid which was washed with EtOAC to give a light yellow solid. The two solids were combined to give 59.4 g of 1d (0.156 mol) total. 1H NMR (CDCl3) δ 2.4 (s, 3H), 5.48 (s, 2H), 7.25-7.58 (m, 3H), 8.61 (s, 1H); MS (CI) m/z 380.9 (MH+)

Workup

  1. customThe resulting mixture became clear then formed precipitate within an hour
  2. filtrationthe yellow solid was filtered
  3. washwashed with cold EtOAc to an almost white solid
  4. washThe filtrate was washed with sat. NaHCO3
  5. dry with materialdried over Na2SO4
  6. customEvaporation
  7. customgave a yellow solid which
  8. washwas washed with EtOAC
  9. customto give a light yellow solid

Sources & evidence

ORD record
ord-d3d7b97593084b58972d48341ea2e50e
Source dataset
uspto-grants-2008_09
Patent number
US07419983B2

Reaction notes

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