Methyl iodide → 5-Methyl-4,5,6,7-tetrahydrothiazolo(5,4-c)pyridine

Thiazolo[5,4-c]pyridine (1.61 g) was dissolved in N,N-dimethylformamide (50 ml), and to the solution methyl iodide (1.50 ml) was added, the resultant mixture was stirred at 80° C. for 4 hours. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in methanol (100 ml), sodium borohydride (1.53 g) was added, and the resultant mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, and a saturated aqueous solution of potassium carbonate and ether were added to the residue to separate an organic layer. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography on silica gel (dichloromethane:methanol=25:1) to obtain the title compound (1.28 g) as a pale yellow oil.

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. dissolutionthe residue was dissolved in methanol (100 ml)
3. additionsodium borohydride (1.53 g) was added
4. concentrationThe reaction mixture was concentrated under reduced pressure
5. additiona saturated aqueous solution of potassium carbonate and ether were added to the residue
6. customto separate an organic layer
7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
8. distillationthe solvent was distilled off under reduced pressure
9. customThe residue was purified by column chromatography on silica gel (dichloromethane:methanol=25:1)

ORD record

ord-a9e06777e3704e78af2ce984d829c01b

Source dataset

uspto-grants-2007_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07192968B2