Ammonium Chloride → Methyl 5-(4,6-dimethoxypyrimidin-5-yl)-5-(1,1-dimethylethylsulfinamido)pentanoate

Temperature

-78 °C

A cooled (−78° C.) solution of 5-bromo-4,6-dimethoxypyrimidine (473 mg; 2.15 mmol) in anh. THF (5 ml), under nitrogen, was treated dropwise with a solution of 1.6 M n-BuLi in hexanes (1.50 ml; 2.40 mmol). The resulting solution was further stirred at −78° C. for 10 min. A solution of methyl 5-((tert-butylsulfinyl)imino)pentanoate (503 mg; 2.15 mmol) in anh. THF (2 ml) was then added to the cooled reaction mixture, and stirring at −78° C. was continued for 60 min. The resulting reaction mixture was treated successively with aq. sat. NH4Cl (15 ml), Et2O (30 ml) and water (15 ml). The separated organic layer was then washed with brine (15 ml), dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (DCM/MeOH=25/1) afforded methyl 5-(4,6-dimethoxypyrimidin-5-yl)-5-(1,1-dimethylethylsulfinamido)pentanoate as a yellow solid. LC-MS (conditions A): tR=0.66 min.; [M+H]+: 374.06 g/mol.

1. stirringstirring at −78° C.
2. waitwas continued for 60 min
3. customThe resulting reaction mixture
4. washThe separated organic layer was then washed with brine (15 ml)
5. dry with materialdried over anh. MgSO4
6. filtrationfiltered
7. concentrationconcentrated to dryness under reduced pressure
8. customPurification by FC (DCM/MeOH=25/1)

ORD record

ord-f2311ef0bcc74d4aaf15b4e3784eee38

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09242970B2