2,3-Lutidine → 5-BROMO-2,3-DIMETHYLPYRIDINE

HRID 1855857Notes

Reaction equation

HRID 1855857 reaction equation
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[Br:9]Br>OS(O)(=O)=O.O=S(=O)=O>[Br:9][C:5]1[CH:4]=[N:3][C:2]([CH3:1])=[C:7]([CH3:8])[CH:6]=1

Participants

4

Reactant 2

HCID 114202,3-LutidineHCID 24408Bromine

Product 1

HCID 114467625-BROMO-2,3-DIMETHYLPYRIDINE

Reagents, catalysts & solvents 1

HCID 24681Fuming sulfuric acidSolvent

Procedure

2,3-Dimethylpyridine is treated with bromine in oleum to give 3-bromo-5,6-dimethylpyridine which is converted into a Grignard reagent, and this is treated with ethyl orthoformate and the product hydrolysed to give 5,6-dimethylpyridine-3-carboxaldehyde. This aldehyde is condensed with malonic acid and the product is hydrogenated and esterified to give ethyl β-(5,6-dimethyl-3-pyridyl)propionate. Substitution of this ester for ethyl β-(3-pyridyl)propionate in the procedure of Example 6 and fusion of the product with 2-(5-methyl-4-imidazolylmethylthio)ethylamine gives 2-[2-(5-methyl-4-imidazolylmethylthio)ethylamino]-5-(5,6-dimethyl-3-pyridylmethyl)-4-pyrimidone.

Sources & evidence

ORD record
ord-a883865757de4d069b83c8f25f5fe8b2
Source dataset
uspto-grants-1980_08
Patent number
US04216318

Reaction notes

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