Sodium Chloride → 1-(2-Methoxy-4-nitrophenyl)-3-methyltetrahydropyrimidin-2(1H)-one

450 mg (3.94 mmol) of 1-methyltetrahydropyrimidin-2(1H)-one in 15 ml of DMF are admixed at 0° C. with 663 mg (5.91 mmol) of potassium tert-butoxide, and the mixture is stirred at room temperature for 30 min. 742 mg (4.33 mmol) of 1-fluoro-2-methoxy-4-nitrobenzene are added and the mixture is stirred at RT. After 2 h, the mixture is admixed with 150 ml of water and 8 ml of saturated aqueous sodium chloride solution, and extracted three times with 30 ml each time of ethyl acetate. The combined organic phases are washed with 30 ml of water and then dried over sodium sulfate. After filtration, the solvents are removed under reduced pressure. The residue is purified by chromatography on silica gel (1:5→1:10 cyclohexane/ethyl acetate). This affords 457 mg (43% of theory) of the desired compound.

1. stirringthe mixture is stirred at RT
2. waitAfter 2 h
3. extractionextracted three times with 30 ml each time of ethyl acetate
4. washThe combined organic phases are washed with 30 ml of water
5. dry with materialdried over sodium sulfate
6. filtrationAfter filtration
7. customthe solvents are removed under reduced pressure
8. customThe residue is purified by chromatography on silica gel (1:5→1:10 cyclohexane/ethyl acetate)

ORD record

ord-6f04d5db2c7843f2a4e356bcd5a47f38

Source dataset

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08198267B2