Methyl iodide → 5-Methyl-4,5,6,7-tetrahydrothiazolo[4,5-c]pyridine

Temperature

80 °C

In N,N-dimethylformamide (80 ml) was dissolved thiazolo[4,5-c]pyridine (700 mg), followed by the addition of methyl iodide (0.65 ml). The resulting mixture was stirred under heat at 80° C. for 4 hours. After concentration of the reaction mixture under reduced pressure, the residue was dissolved in water (100 ml). Sodium borohydride (583 mg) was added to the resulting solution, followed by stirring at room temperature for 1 hour. After the addition of a saturated aqueous solution of potassium carbonate, the resulting mixture was extracted with ether. The organic layer thus extracted was dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column (methylene chloride:methanol=25:1), whereby the title compound (596 mg) was obtained as a colorless oil.

1. stirringby stirring at room temperature for 1 hour
2. extractionthe resulting mixture was extracted with ether
3. extractionThe organic layer thus extracted
4. dry with materialwas dried over anhydrous sodium sulfate
5. distillationdistilled under reduced pressure
6. customto remove the solvent
7. customThe residue was purified by chromatography on a silica gel column (methylene chloride:methanol=25:1), whereby the title compound (596 mg)
8. customwas obtained as a colorless oil

ORD record

ord-ede08ee8c3084a36a44ca0dd9c3f63a0

Source dataset

uspto-grants-2004_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06747023B1