Chloroacetaldehyde → HCID 13394201, compound

Temperature

80 °C

A mixture of 5 g (32 mmole) of 4-amino-6-methyl-2-methylthiopyrimidine and 10 g (64 mmole) of a 50% aqueous solution of chloroacetaldehyde was heated at 80° C. for one hour. The mixture was cooled with an ice bath and immediately neutralized with sodium bicarbonate. The mixture was extracted with chloroform and the extracts were dried over magnesium sulfate and evaporated to provide an oil. The oil was extracted with hot ethyl acetate, and the extrats were filtered and then evaporated. The residue was dissolved in hot benzene, treated with decolorizing charcoal, and filtered, and the filtrate was evaporated. The residue thereby obtained was dissolved in hot diethyl ether, treated with decolorizing charcoal, and filtered, the filtrate then being evaporated. The residue obtained was recrystallized first from a benzene/hexane mixture and then from cyclohexane, each time accompanied by treatment with decolorizing charcoal. The solid was purified on a preparative scale high pressure liquid chromatograph using ethyl acetate as the eluent. The solid obtained was recrystallized from hexanes to give white crystals of 7-methyl-5-methylthioimidazo[1,2-c]pyrimidine, m.p. 67°-69° C. Analysis: Calculated for C8H9N3S: %C,53.6; %H,5.1; %N,23.4; Found: %C,53.2; %H,5.0; %N,23.8.

1. temperatureThe mixture was cooled with an ice bath
2. extractionThe mixture was extracted with chloroform
3. dry with materialthe extracts were dried over magnesium sulfate
4. customevaporated
5. customto provide an oil
6. extractionThe oil was extracted with hot ethyl acetate
7. filtrationthe extrats were filtered
8. customevaporated
9. dissolutionThe residue was dissolved in hot benzene
10. additiontreated with decolorizing charcoal
11. filtrationfiltered
12. customthe filtrate was evaporated
13. customThe residue thereby obtained
14. filtrationfiltered
15. customthe filtrate then being evaporated
16. customThe residue obtained
17. customwas recrystallized first from a benzene/hexane mixture
18. customThe solid was purified on a preparative scale high pressure liquid chromatograph
19. customThe solid obtained
20. customwas recrystallized from hexanes

ORD record

ord-b8305e15230547f1a25839f97bfd69a4

Source dataset

uspto-grants-1985_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04503050