Bromine → 5-Bromo-3-methyl-2-methylsulfanyl-6-pyridin-4-ylpyrimidin-4-one

HRID 2229782Notes

Reaction equation

HRID 2229782 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[CH:6]=[C:5]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[N:4]=[C:3]1[S:15][CH3:16].[Br:17]Br>C(O)(=O)C>[CH3:1][N:2]1[C:7](=[O:8])[C:6]([Br:17])=[C:5]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[N:4]=[C:3]1[S:15][CH3:16]

Participants

4

Reactant 2

HCID 24408BromineHCID 155215183-methyl-2-methylsulfanyl-6-pyridin-4-yl-3H-pyrimidin-4-one

Product 1

HCID 187680025-Bromo-3-methyl-2-methylsulfanyl-6-pyridin-4-ylpyrimidin-4-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3-Methyl-6-(4-pyridyl)-2-methylthio-4(3H)-pyrimidinone (1.00 g 4.29 mmol) was dispersed in acetic acid (24 ml) and to the clear solution Bromine (0.5 ml, 1.5 g 9.38 mmol) was added. The reaction mixture stirred at room temperature for 24 h. The mixture was concentrated and the residue was co-evaporated with toluene until all bromine is removed. The crude compound is ready to use in next step. MS(m/z): 312 and 314. C10H11BrN3OS requir. 311 and 313. 1H-NMR(DMSO-d6):d 8.75 (m, 2H, pyridyl) 8.19 (m, 2H, pyridyl), 3.67 (s, 3H, N—CH3), 2.80 (s, 3H, S—CH3).

Workup

  1. additionwas added
  2. concentrationThe mixture was concentrated
  3. customis removed

Sources & evidence

ORD record
ord-4381cb533bf941149790156f07717e74
Source dataset
uspto-grants-2002_07
Patent number
US06420385B1

Reaction notes

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