Réaction #68678

Équation de réaction

tert-butyl (6-formyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate

methylmagnesium bromide

NH4Cl

→

tert-butyl (6-(1-hydroxyethyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate

Rendement 95.5%

Solvants

THF

Conditions de réaction

Traitement

1. 1
   Températurethe reaction mixture was warmed to 0° C. over 1 h
2. 2
   workup.WAITAfter 1 h the reaction mixture based on LC-MS
3. 3
   ExtractionThe aqueous phase was extracted 3× with DCM
4. 4
   Séchagethe organic layer was dried over Na2SO4
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated under reduced pressure

Mode opératoire

In a 10 mL round bottom flask under N2 was dissolved tert-butyl (6-formyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate (200 mg, 721 μmol) in 3 mL of THF then cooled at −78° C. and treated with methylmagnesium bromide (721 μl, 2164 μmol). After 30 minutes, the reaction mixture was warmed to 0° C. over 1 h. After 1 h the reaction mixture based on LC-MS was neutralized with NH4Cl (sat.). The aqueous phase was extracted 3× with DCM then the organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The crude tert-butyl (6-(1-hydroxyethyl)-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methylcarbamate (202 mg, 95.5% yield) was used without further purification in the next step. MS m/z=294.4 [M+1]+. Calc'd for C13H19N5O3: 293.3.

Source