Phosphorus oxychloride → 4-Chloro-2-(methylsulfanyl)pyrimidine-5-carbonitrile

A stirred solution of 4-hydroxy-2-(methylthio)pyrimidine-5-carbonitrile (British patent GB901749) (1.00 g, 5.98 mmol) in POCl3 (5 mL) was heated to reflux for 2 h. The reaction mixture was concentrated in vacuo and the residue quenched with ice (100 g). The solution was then basified to pH 8 with sat. aq NaHCO3 and extracted with ethyl acetate (3×50 mL). The combined ethyl acetate layers were washed with water (20 mL), brine (10 mL), dried over Na2SO4, filtered and concentrated to give the title compound.

1. temperatureto reflux for 2 h
2. concentrationThe reaction mixture was concentrated in vacuo
3. customthe residue quenched with ice (100 g)
4. extractionextracted with ethyl acetate (3×50 mL)
5. washThe combined ethyl acetate layers were washed with water (20 mL), brine (10 mL)
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated

ORD record

ord-fbb8a9767afe4b50ac6f81b152240b6c

Source dataset

uspto-grants-2006_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07053089B2