Diisopropylethylamine → HCID 68686581, compound

Temperature

0 °C

2,4-dichloro-5-nitropyrimidine (Aldrich; 10 g, 0.052 mol) was dissolved in THF (250 mL). To this was added DIPEA (11 mL, 0.062 mol) and the reaction cooled to 0° C. Methyl3-(cyclohexylamino)propanoate (9.5 g, 0.052 mol) in THF (30 mL) was slowly added. The cooling bath was removed and the reaction was stirred at room temperature for 1 hour. To the reaction mixture was added saturated NH4OH(aq) (100 mL), and the reaction heated at 55° C. for 4 hours using a dry ice condenser. The reaction mixture was extracted with DCM (3×100 ml), and combined organic extracts dried and evaporated. The residue was dissolved in methanol (200 mL). Ammonium formate (33 g, 0.52 mol) and 10% palladium (1.5 g) were added. The reaction was heated at reflux for 5 hours, filtered and the methanol evaporated to yield a dark orange solid, which was quenched with 2.0 N NaOH(aq) (100 mL), extracted with DCM (3×150 mL), and combined extracts dried and evaporated to yield an orange solid. Hot acetonitrile was added, this was stirred and then sonicated to give a precipitate that was filtered and dried to yield the title compound as a yellow solid (7.5 g, 55%).

1. customThe cooling bath was removed
2. additionTo the reaction mixture was added saturated NH4OH(aq) (100 mL)
3. temperaturethe reaction heated at 55° C. for 4 hours
4. extractionThe reaction mixture was extracted with DCM (3×100 ml)
5. customdried
6. customevaporated
7. dissolutionThe residue was dissolved in methanol (200 mL)
8. temperatureThe reaction was heated
9. temperatureat reflux for 5 hours
10. filtrationfiltered
11. customthe methanol evaporated
12. customto yield a dark orange solid, which
13. customwas quenched with 2.0 N NaOH(aq) (100 mL)
14. extractionextracted with DCM (3×150 mL)
15. customdried
16. customevaporated
17. customto yield an orange solid
18. stirringthis was stirred
19. customsonicated
20. customto give a precipitate that
21. filtrationwas filtered
22. customdried

ORD record

ord-a93a68e7ae4f41f8b2f93cf70a0c5a5b

Source dataset

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07709471B2