Dimethylformamide → 5-{[(4-Chlorophenyl)sulfanyl](2,5-difluorophenyl)methyl}pyrimidine

The 5-[(2,5-difluorophenyl)-hydroxymethyl]pyrimidine (111 mg, 0.5 mmol) obtained in Referential Example 12 was dissolved in thionyl chloride (1.0 ml). A catalytic amount of dimethylformamide was added and the resulting mixture was stirred for 16 hours. The reaction mixture was concentrated under reduced pressure. To the residue was added dioxane, and the resulting mixture was concentrated further. The residue was dissolved in dimethylformamide (5 ml), followed by the addition of 4-chlorobenzenethiol (108 mg, 0.75 mmol) and potassium carbonate (414 mg, 3.0 mmol) under a nitrogen atmosphere. The resulting mixture was stirred at 50° C. for 1 hour. After the reaction mixture was cooled to room temperature, diethyl ether (50 ml) was added thereto. The resulting mixture was washed with water and brine. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel chromatography (hexane:ethyl acetate=4:1) to give a mixture (202 mg) of the title compound and an unidentified compound as an oil.

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. additionTo the residue was added dioxane
3. concentrationthe resulting mixture was concentrated further
4. dissolutionThe residue was dissolved in dimethylformamide (5 ml)
5. stirringThe resulting mixture was stirred at 50° C. for 1 hour
6. washThe resulting mixture was washed with water and brine
7. dry with materialThe organic layer was dried over magnesium sulfate
8. concentrationconcentrated under reduced pressure

ORD record

ord-c8e1ccdef8d640378218851f72e6934b

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07932271B2