Bromine → 2-benzyl-5-bromo-3-methylpyrimidin-4(3H)-one

HRID 1993341Notes

Reaction equation

HRID 1993341 reaction equation
[Br:1]Br.[CH2:3]([C:10]1[N:15]([CH3:16])[C:14](=[O:17])[CH:13]=[CH:12][N:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl>[CH2:3]([C:10]1[N:15]([CH3:16])[C:14](=[O:17])[C:13]([Br:1])=[CH:12][N:11]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 57445390HCID 57445390, compound

Product 1

HCID 574453912-benzyl-5-bromo-3-methylpyrimidin-4(3H)-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Br2 (2.62 mL, 52 mmol) was added to 2-benzyl-3-methyl-3H-pyrimidin-4-one (Step 2, 9.3 g, 47 mmol) in CHCl3 (100 mL) and sat NaHCO3 (100 mL). After 30 min, the organic layer was separated, dried (Na2SO4) and filtered through a plug of silica. The filtrate was concentrated under reduced pressure, and azeotroped with CHCl3 (2×). The crude compound was dried under high vacuum for 16 h to provide the title compound. MS (ESI pos. ion) m/z: 279.0, 281.1. Calc'd for C12H11BrN2O: 278.01.

Workup

  1. customthe organic layer was separated
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered through a plug of silica
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customazeotroped with CHCl3 (2×)
  6. dry with materialThe crude compound was dried under high vacuum for 16 h

Sources & evidence

ORD record
ord-58586560bc364d57947d449f3d53b2f7
Source dataset
uspto-grants-2010_01
Patent number
US07652009B2

Reaction notes

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