Ethyl Acetate → HCID 18362954, compound

Temperature

50 °C

3,6-Dimethyl-5-formyl-1-(1-methylethyl)pyrimidine-2,4-dione (J. Med. Chem., 1995, 38, 2557; 1.70 g) was dissolved in chloroform (25 ml) and the solution was heated to 50° C. A solution of bromine (0.413 ml) in chloroform (20 ml) was added dropwise to the aldehyde solution over 24 minutes. The reaction was maintained at 50° C. for a further 15 minutes, then allowed to cool to ambient temperature. The reaction mixture was diluted with dichloromethane and was washed successively with water, dilute sodium thiosulphate solution (twice) and brine. The resultant solution was dried, filtered and evaporated to a crude oil which was dissolved in ethanol (50 ml). Triethylamine (3.38 ml) was added to the solution followed by 2-aminoindane (1.49 g) and the mixture was stirred under nitrogen overnight. The reaction mixture was filtered, the white solid collected was washed with a little ethanol and the filtrate was evaporated to give a brown oil. Ethyl acetate was added to the oil and the resultant precipitate was collected by filtration and was washed with a little ethyl acetate. The filtrate was washed with hydrochloric acid (HCl) (2.5 M) and then brine. The resultant ethyl acetate phase was dried, filtered and evaporated to an oil. The oil was purified by chromatography, eluting with isohexane: acetone (4:1) to give a solid which was triturated with hot ethyl acetate:isohexane (3:1) to give the subtitle compound (0.50 g).

1. temperatureThe reaction was maintained at 50° C. for a further 15 minutes
2. temperatureto cool to ambient temperature
3. washwas washed successively with water, dilute sodium thiosulphate solution (twice) and brine
4. dry with materialThe resultant solution was dried
5. filtrationfiltered
6. customevaporated to a crude oil which
7. dissolutionwas dissolved in ethanol (50 ml)
8. additionTriethylamine (3.38 ml) was added to the solution
9. filtrationThe reaction mixture was filtered
10. customthe white solid collected
11. washwas washed with a little ethanol
12. customthe filtrate was evaporated
13. customto give a brown oil
14. filtrationthe resultant precipitate was collected by filtration
15. washwas washed with a little ethyl acetate
16. washThe filtrate was washed with hydrochloric acid (HCl) (2.5 M)
17. dry with materialThe resultant ethyl acetate phase was dried
18. filtrationfiltered
19. customevaporated to an oil
20. customThe oil was purified by chromatography
21. washeluting with isohexane: acetone (4:1)
22. customto give a solid which
23. customwas triturated with hot ethyl acetate:isohexane (3:1)

ORD record

ord-69e6e609cb924978b8bcb685a1fbe437

Source dataset

uspto-grants-2001_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06229013B1