Methyl iodide → HCID 59255062, compound

Temperature

0 °C

To a stirred solution of ethyl 1-isopropyl-6-methyl-2-oxo-1,2-dihydropyridine-3-carboxylate as prepared in Example 1(5) (515 mg, 2.0 mmol) in tetrahydrofuran (3 mL) was added a solution of lithium diisopropylamide (2.0M, 1.0 mL, 1.0 mmol) dropwise at −30° C. over 40 min. After addition, the mixture was stirred at 0° C. for 3 h. Then, methyl iodide (426 mg, 3.0 mmol) was added at 0° C., and the mixture was stirred at room temperature for 16 h. The mixture was quenched with water (5.0 mL), and extracted with dichloromethane (30 mL×3). The combined organic layers were dried over magnesium sulfate and concentrated in vacuo. The residue was purified with plate TLC eluting with n-hexane/ethyl acetate (v/v=2/1) to give 110 mg (23%) of the title compound as yellow oil.

1. additionAfter addition
2. stirringthe mixture was stirred at room temperature for 16 h
3. customThe mixture was quenched with water (5.0 mL)
4. extractionextracted with dichloromethane (30 mL×3)
5. dry with materialThe combined organic layers were dried over magnesium sulfate
6. concentrationconcentrated in vacuo
7. customThe residue was purified with plate TLC
8. washeluting with n-hexane/ethyl acetate (v/v=2/1)

ORD record

ord-def6f81c669346f38898f730da1a01a9

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08362038B2