Phosphorus oxychloride → 4-Chloro-6-(chloromethyl)-2-(methylthio)pyrimidine

A mixture of 35 g (0.18 mole) of the known compound 6-chloromethyl-2-methylthiopyrimidin-4-one and 300 ml of phosphorous oxychloride was heated at reflux for 3.5 hours, cooled and evaporated. The mixture was poured into 600 ml of an ice-water mixture and the mixture was extracted with four 200 ml portions of chloroform. The combined extracts were washed sequentially with two 200 ml portions of water, 20 ml of saturated aqueous sodium bicarbonate solution and 200 ml of saturated aqueous sodium chloride solution, and were then dried over magnesium sulfate and evaporated. The residue was distilled at reduced pressure to provide 4-chloro-6-chloromethyl-2-methylthiopyrimidine as a yellow liquid, b.p. 90°-95° C./0.15 mm Hg. The structural assignment was confirmed by infrared and nuclear magnetic resonance spectral analyses.

1. temperaturewas heated
2. temperatureat reflux for 3.5 hours
3. temperaturecooled
4. customevaporated
5. additionThe mixture was poured into 600 ml of an ice-water mixture
6. extractionthe mixture was extracted with four 200 ml portions of chloroform
7. washThe combined extracts were washed sequentially with two 200 ml portions of water, 20 ml of saturated aqueous sodium bicarbonate solution and 200 ml of saturated aqueous sodium chloride solution
8. dry with materialwere then dried over magnesium sulfate
9. customevaporated
10. distillationThe residue was distilled at reduced pressure

ORDレコード

ord-43f90499fdf94719a9d96d8322e81787

出典データセット

uspto-grants-1984_10

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US04478835