Reaction #74062

Reaction equation

sodium hydroxide

methyl 2-(5-bromopyrimidin-4-ylthio)acetate

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-naphthonitrile

sodium carbonate

→

2-(5-(4-cyanonaphthalen-1-yl)pyrimidin-4-ylthio)acetic acid

Yield 53.0%

Solvents

dioxane

Conditions

Workup

1. 1
   Temperatureto cool to room temperature
2. 2
   WashThe mixture was washed with ethyl acetate (2×20 mL)
3. 3
   Otherresulting in formation of a precipitate which
4. 4
   Otherwas isolated by filtration
5. 5
   Otherdried under vacuum

Procedure

A mixture of methyl 2-(5-bromopyrimidin-4-ylthio)acetate (220 mg, 0.84 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-naphthonitrile (237 mg, 0.85 mmol) palladium tetrakis triphenylphoshine (46 mg, 0.04 mmol) and aqueous sodium carbonate solution (2M, 1.5 mL, 3 mmol) in dioxane (3 mL) was heated to 100° C. for 5 hours. The reaction mixture was allowed to cool to room temperature and aqueous sodium hydroxide solution added (1M, 30 mL). The mixture was washed with ethyl acetate (2×20 mL), and the aqueous layer acidified to pH 4 resulting in formation of a precipitate which was isolated by filtration and dried under vacuum to yield 2-(5-(4-cyanonaphthalen-1-yl)pyrimidin-4-ylthio)acetic acid (143 mg, 53%).

Source