Trifluoromethanesulfonic acid → 3-(3-bromo-2-methylphenyl)pyrimidine-2,4(1H,3H)-dione

HRID 523277Notes

Reaction equation

HRID 523277 reaction equation
[Br:1][C:2]1[C:3]([CH3:25])=[C:4]([N:8]2[C:13](=[O:14])[CH:12]=[CH:11][N:10](CC3C=CC(OC)=CC=3)[C:9]2=[O:24])[CH:5]=[CH:6][CH:7]=1.FC(F)(F)S(O)(=O)=O>C(O)(C(F)(F)F)=O>[Br:1][C:2]1[C:3]([CH3:25])=[C:4]([N:8]2[C:13](=[O:14])[CH:12]=[CH:11][NH:10][C:9]2=[O:24])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 62406Trifluoromethanesulfonic acidHCID 1177754293-(3-bromo-2-methylphenyl)-1-(4-methoxybenzyl)pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 1177608363-(3-bromo-2-methylphenyl)pyrimidine-2,4(1H,3H)-dioneYield 101.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 3-(3-bromo-2-methylphenyl)-1-(4-methoxybenzyl)pyrimidine-2,4(1H,3H)-dione (0.87 g, 2.17 mmol) in TFA (5.5 mL) was treated with trifluoromethanesulfonic acid (0.55 mL) and the mixture was stirred at room temperature overnight. The mixture was slowly poured onto ice and stirred while warming to room temperature. The precipitate was collected by filtration, washed with water and dried to provide 3-(3-bromo-2-methylphenyl)pyrimidine-2,4(1H,3H)-dione as a purple solid (0.62 g, 96% yield). Mass spectrum m/z 281, 283 (M+H)+. 1H NMR (400 MHz, DMSO-d6) δ 11.36 (d, J=4.4 Hz, 1H), 7.67 (dd, J=6.5, 2.8 Hz, 1H), 7.60 (dd, J=7.7, 5.9 Hz, 1H), 7.27-7.21 (m, 2H), 5.72 (dd, J=7.7, 1.3 Hz, 1H), 2.07 (s, 3H).

Workup

  1. additionThe mixture was slowly poured onto ice
  2. stirringstirred
  3. temperaturewhile warming to room temperature
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-628030cdd7274a5aabb63e1c586dbcc0
Source dataset
uspto-grants-2016_05
Patent number
US09334290B2

Reaction notes

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