Tert-Butyl hypochlorite → 2-[(4,6-Dimethoxypyrimidin-2-yl)-methylthiomethyl]-6-methoxymethylaniline

Temperatur

-70 °C

2-Methoxymethylaniline (0.68 g, 4.96 mmol) was dissolved in dichloromethane (50 ml) and the solution was cooled to −70° C. To the cooled solution a solution of tert-butyl hypochlorite (0.54 g, 4.96 mmol) in dichloromethane (1 ml) was added dropwise and the solution was stirred at −70° C. for 10 minutes. To the obtained reaction solution a solution of 2-methylthiomethyl-4,6-dimethoxypyrimidine (0.893 g, 4.46 mmol) in dichloromethane (5 ml) was added dropwise and the solution was stirred at −70° C. for 30 minutes. To the obtained reaction solution a 28% methanol solution of sodium methoxide (4 ml) was added and the solution was stirred until its temperature reached room temperature. Water was added to the reaction solution and the organic layer was separated. The water layer was further extracted twice with dichloromethane. The organic layer was washed with water and dried. Then dichloromethane was distilled off under reduced pressure and the obtained oily substance was purified by column chromatography using 1:6 mixed solvent of ethyl acetate and hexane as eluent to obtain 2-[(4,6-dimethoxypyrimidin-2-yl)-methylthiomethyl]-6-methoxymethylaniline (0.88 g, yield 53%) as oily substance;

1. additionwas added dropwise
2. stirringthe solution was stirred at −70° C. for 30 minutes
3. additionwas added
4. stirringthe solution was stirred until its temperature
5. customreached room temperature
6. customthe organic layer was separated
7. extractionThe water layer was further extracted twice with dichloromethane
8. washThe organic layer was washed with water
9. customdried
10. distillationThen dichloromethane was distilled off under reduced pressure
11. customthe obtained oily substance was purified by column chromatography

ORD-Eintrag

ord-8f4ca55198c64fdfb6527531970c3dc7

Quelldatensatz

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07772395B2