Sodium Methoxide → 2-(4-Bromo-3-methylphenyl)pyrimidine

HRID 1956963Notes

Reaction equation

HRID 1956963 reaction equation
[CH3:1][C:2]1[C:7](C(N)=O)=[C:6]([C:11]([NH2:13])=O)[CH:5]=[CH:4][C:3]=1[Br:14].C[O-].[Na+]>CO>[Br:14][C:3]1[CH:4]=[CH:5][C:6]([C:11]2[N:13]=[CH:5][CH:6]=[CH:11][N:13]=2)=[CH:7][C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 18663194HCID 18663194, compound

Product 1

HCID 186631912-(4-Bromo-3-methylphenyl)pyrimidineYield 300.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5.0 g (23.46 mmol) of the title compound of Step A in 15 mL of methanol ("MeOH"), 7.94 g (35.2 mmol) of the title compound of Step B and 1.9 g (35.2 mmol) of sodium methoxide were added and the mixture stirred at room temperature under argon for 1 hr. The solution was then refluxed for 4 hrs and concentrated to about 10 mL. The residue was then added to 200 mL of water and extracted with 4×150 mL of ethyl acetate ("EtOAc"). The combined organic extracts were washed once with water and dried and evaporated. The residue was chromatographed on 100 g of silica gel using Hexanes/EtOAc 4:1 to provide 1.65 g (28%) of the title compound of this step as a white solid.

Sources & evidence

ORD record
ord-74794e48b5f74904bb47b56016255697
Source dataset
uspto-grants-1998_07
Patent number
US05780473

Reaction notes

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