Reaktion #2476093

Reaktionsgleichung

4,6-dichloro-2-[(2,3-difluorobenzyl)thio]pyrimidine

product

N-[2-[[(2,3-difluorophenyl)methyl]thio]-6-[2-hydroxy-1-(hydroxymethyl)ethoxy]-4-pyrimidinyl]-1-azetidinesulfonamide

(trans)-cyclopentane-1,2-diol

NaH

→

subtitle compound

(trans)-2-{6-Chloro-2-[(2,3-difluorobenzyl)thio]pyrimidin-4-yl}cyclopentanol

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mixture was then partitioned between DCM (150 ml) and H2O (100 ml)
2. 2
   SonstigeThe organics were separated
3. 3
   Extraktionthe aqueous layer was re-extracted with DCM (2×150 ml)
4. 4
   Trocknendried (MgSO4)
5. 5
   Sonstigethe resulting clear oil was purified by column chromatography on silica gel EtOAc/iso-Hexane (2:8)

Vorschrift

To a solution of 4,6-dichloro-2-[(2,3-difluorobenzyl)thio]pyrimidine (the product of example 1 step 2.3 g) and (trans)-cyclopentane-1,2-diol (1 g) in THF (50 ml) was added NaH (0.30 g) slowly and the reaction was then allowed to stir for 18 h at RT. The reaction mixture was then partitioned between DCM (150 ml) and H2O (100 ml). The organics were separated and the aqueous layer was re-extracted with DCM (2×150 ml). Organics were combined, dried (MgSO4) and reduced in vacuo and the resulting clear oil was purified by column chromatography on silica gel EtOAc/iso-Hexane (2:8) to give the subtitle compound as a clear colourless oil. Yield 0.94 g

Quelle