Reaktion #309336

Reaktionsgleichung

4-chloro-1H-pyrrolo-[2,3-d]pyrimidine

KO-t-Bu

THF

benzenemethanethiol

→

product

Ausbeute 79.0%

4-(Benzylsulfanyl)-7H-pyrrolo[2,3-d]pyrimidine

Ausbeute 79.0%

Lösungsmittel

isopropyl alcohol

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was heated
2. 2
   Temperaturthe reaction mixture was cooled
3. 3
   Sonstigesolvent was removed in vacuo
4. 4
   workup.ADDITIONTo the residue was added water (300 mL)
5. 5
   Filtrationthe solution was filtered
6. 6
   Sonstigeto collect the resulting white solid
7. 7
   WaschenThe solid was washed with diethyl ether and MeOH
8. 8
   Sonstigedried under vacuum

Vorschrift

To a round bottomed flask with a stir bar was added 4-chloro-1H-pyrrolo-[2,3-d]pyrimidine (5.07 g, 33.0 mmol), 1.00 M of KO-t-Bu in THF (49.5 mL, 49.5 mmol), and benzenemethanethiol (5.81 mL, 49.5 mmol) in isopropyl alcohol (350 mL). The reaction mixture was heated to reflux at 85° C. under an atmosphere of nitrogen. After 48 h, the reaction mixture was cooled and solvent was removed in vacuo. To the residue was added water (300 mL) and the solution was filtered to collect the resulting white solid. The solid was washed with diethyl ether and MeOH and dried under vacuum to afford the product as a white solid (6.29 g, 79% yield). LC/MS: Rt=1.68 min, ES+ 242 (FA standard). Reference: Pathak, A. K., Pathak, V., Seitz, L. E., Suling, W. J., Reynolds, R. C. J. Med. Chem., 2004, 47, 273-276.

Quelle