Hydrogen Bromide → 6-bromo-2-methyl-5-nitro-3H-pyrimidin-4-one

HRID 841010Notes

Reaction equation

HRID 841010 reaction equation
[BrH:1].[CH3:2][C:3]1[N:8]=[C:7]([O:9]C)[C:6]([N+:11]([O-:13])=[O:12])=[C:5](Cl)[N:4]=1>C(O)(=O)C>[Br:1][C:5]1[N:4]=[C:3]([CH3:2])[NH:8][C:7](=[O:9])[C:6]=1[N+:11]([O-:13])=[O:12]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 156459054-Chloro-6-methoxy-2-methyl-5-nitropyrimidine

Product 1

HCID 1356171936-bromo-2-methyl-5-nitro-3H-pyrimidin-4-oneYield 69%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

56.6 ml (503 mmol) of hydrobromic acid solution (48% in water) were added dropwise to a solution of 20.5 g (101 mmol) of the 2-methyl-4-methoxy-5-nitro-6-chloro-pyrimidine [Helv. (1958), 41, 1806] in 450 ml of acetic acid and the reaction mixture was stirred at room temperature for 44 hours. It was then evaporated under reduced pressure and the residue formed poured into 500 ml of an ice/water mixture and extracted 3 times with 500 ml of dichloromethane. The combined dichloromethane phases were washed with 100 ml of water and evaporated under reduced pressure. There were thus obtained 16.3 g (69.6 mmol, yield 69%) of the 6-bromo-2-methyl-5-nitro-3H-pyrimidin-4-one as light yellow solid, which was used without further purification.

Workup

  1. customIt was then evaporated under reduced pressure
  2. customthe residue formed
  3. extractionextracted 3 times with 500 ml of dichloromethane
  4. washThe combined dichloromethane phases were washed with 100 ml of water
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-19a95ea51f4c422392e9e46ac0a1522b
Source dataset
uspto-grants-2002_04
Patent number
US06369222B1

Reaction notes

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