Réaction #421307

Équation de réaction

1-(2-(2-chloro-6-morpholino-9H-purin-9-yl)ethyl)cyclopropanol

N,N,N′,N′-tetramethylethylene-diamine

n-butyllithium

hexane

1-chloro-2-iodoethane

→

1-(2-(2-chloro-8-iodo-6-morpholino-9H-purin-9-yl)ethyl)cyclopropanol

Rendement 71.9%

Solvants

THF

Conditions de réaction

Traitement

1. 1
   AutreThe mixture was quenched with a saturated solution of NH4Cl
2. 2
   workup.ADDITIONdiluted with ethyl acetate
3. 3
   ExtractionThe aqueous layer was extracted into ethyl acetate (3×)
4. 4
   Séchagethe combined organics were dried over sodium sulfate
5. 5
   Filtrationfiltered
6. 6
   Autreabsorbed onto celite for purification by flash chromatography

Mode opératoire

A solution of 1-(2-(2-chloro-6-morpholino-9H-purin-9-yl)ethyl)cyclopropanol (220 mg, 0.68 mmol) and N,N,N′,N′-tetramethylethylene-diamine (0.15 mL, 1.0 mmol) in THF (4.9 mL) was cooled to −42° C. and treated with a solution of 2.5M n-butyllithium in hexane (1.5 mL, 3.7 mmol) dropwise over 5 minutes. After 30 minutes at −42° C., 1-chloro-2-iodoethane (0.31 mL, 3.3 mmol) was added and the reaction mixture was slowly warmed to 0° C. over 1 hr. The mixture was quenched with a saturated solution of NH4Cl, and diluted with ethyl acetate. The aqueous layer was extracted into ethyl acetate (3×), and the combined organics were dried over sodium sulfate, filtered, and absorbed onto celite for purification by flash chromatography to afford 1-(2-(2-chloro-8-iodo-6-morpholino-9H-purin-9-yl)ethyl)cyclopropanol as a colorless oil (220 mg, 71%). LC/MS (ESI+): m/z 450 (M+H)

Source