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

HRID 2054520Notes

Reaction equation

HRID 2054520 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 2.422 (s, 3H), 5.478 (s, 2H), 7.246-7.582 (m, 3H), 8.611 (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-d9ba77f1e9714708aea903a1b31c12d6
Source dataset
uspto-grants-2008_02
Patent number
US07329669B2

Reaction notes

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