Iodine → 2-Iodo-3-methoxypyrazine

To 20 ml of an anhydrous THF solution of 1.3 g of diisopropylamine was added 4.8 ml (2.5 M hexane solution) of n-butyllithium at −78° C., and the mixture was stirred at that temperature for 20 minutes. To the reaction mixture was added 10 ml of a THF solution of 1.1 of 2-methoxypyrazine, followed by stirring at −78° C. for 1 hour. To the reaction mixture was further added 10 ml of a THF solution of 4.0 g of iodine, followed by stirring for 4 hours while gradually elevating the temperature to room temperature. The reaction mixture was diluted with ethyl acetate, washed successively with a saturated sodium thiosulfate aqueous solution and a saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate. The solvent was evaporated, and the residue was subjected to silica gel column chromatography using chloroform as a developing solution. The fraction containing the desired compound was concentrated to give 0.49 g of the title compound.

1. stirringby stirring at −78° C. for 1 hour
2. stirringby stirring for 4 hours
3. customto room temperature
4. washwashed successively with a saturated sodium thiosulfate aqueous solution
5. dry with materiala saturated sodium chloride aqueous solution, and dried over anhydrous sodium sulfate
6. customThe solvent was evaporated
7. additionThe fraction containing the desired compound
8. concentrationwas concentrated

ORD record

ord-6c1e1ba4d4e74829bcb297d088ac53b0

Source dataset

uspto-grants-2001_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06169086A