4,6-Dichloropyrimidine → Methyl 3-(6-chloropyrimidin-4-ylamino)benzoate

Temperature

110 °C

To a stirred solution of 4,6-dichloropyrimidine (0.5 g, 3.7 mmol) in n-butanol (10 mL) was added methyl 3-aminobenzoate (0.498 g, 3.7 mmol) and DIPEA (0.65 g, 5.0 mmol) and the reaction mixture was heated at 110° C. for 12 h. It was cooled and excess n-butanol was removed under reduced pressure. The residue was extracted with EtOAc (2×30 mL) and the combined EtOAc extract was washed with water (5 mL), brine (2.5 mL), dried over Na2SO4 and concentrated under reduced pressure. The residue was stirred with pet ether (30 mL) for 30 min, the pet ether removed by decantation and the solid obtained was dried under high vacuum to give methyl 3-(6-chloropyrimidin-4-ylamino)benzoate (0.3 g, 34%) as light brown solid.

1. temperatureIt was cooled
2. customexcess n-butanol was removed under reduced pressure
3. extractionThe residue was extracted with EtOAc (2×30 mL)
4. extractionthe combined EtOAc extract
5. washwas washed with water (5 mL), brine (2.5 mL)
6. dry with materialdried over Na2SO4
7. concentrationconcentrated under reduced pressure
8. customthe pet ether removed by decantation
9. customthe solid obtained
10. customwas dried under high vacuum

ORD record

ord-595b11608bc04744901b6391c6c0ec5a

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09040541B2