Phosphorus oxychloride → 4-Chloro-6-(chloromethyl)pyrimidin-2-amine

47.9 Parts of 2-amino-4-chloromethyl-6-hydroxypyrimidine was added portionwise to 410 parts of phosphorus oxychloride with stirring. The mixture was placed in an oil bath at 130° C. and stirred until all the solid had dissolved and then for a further 10 minutes. The solution was cooled and the excess of phosphorus oxychloride was removed in vacuo. The residual viscous oil was poured onto 300 parts of ice with stirring and the pH of the resulting mixture was adjusted to pH 8 by the portionwise addition of solid sodium bicarbonate. The mixture was extracted four times with diethyl ether. The ether extracts were combined, dried over anhydrous magnesium sulphate and evaporated to give a pale-yellow solid. Recrystallisation from carbon tetrachloride gave pure 2-amino-4-chloro-6-chloromethylpyrimidine m.p. 126°-128° C.

1. customThe mixture was placed in an oil bath at 130° C.
2. stirringstirred until all the solid
3. dissolutionhad dissolved
4. temperatureThe solution was cooled
5. customthe excess of phosphorus oxychloride was removed in vacuo
6. additionThe residual viscous oil was poured onto 300 parts of ice
7. stirringwith stirring
8. additionthe pH of the resulting mixture was adjusted to pH 8 by the portionwise addition of solid sodium bicarbonate
9. extractionThe mixture was extracted four times with diethyl ether
10. dry with materialdried over anhydrous magnesium sulphate
11. customevaporated
12. customto give a pale-yellow solid
13. customRecrystallisation from carbon tetrachloride

ORD record

ord-c5ccdb6526a343d180e97ac51b4a58da

Source dataset

uspto-grants-1988_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04723006